Organic electroluminescent element, organic electroluminescent device, electronic device, light-emitting body, solar cell, and light sensor

Abstract

An organic electroluminescent element (1) having an anode (3), a cathode (4), and a light-emitting region (5) disposed between the anode (3) and the cathode (4), the light-emitting region (5) including a first sensitizing layer (51) and a first light-emitting layer (52), the first sensitizing layer (51) containing a first host material and a first sensitizing material, the first light-emitting layer (52) containing a second host material and a first light-emitting compound, and the second sensitizing layer (51) containing a second host material and a second light-emitting compound. The first host material and the second host material are different from each other, the first sensitizing material and the first light-emitting compound are different from each other, and the difference [Delta] ST (G1) between the lowest excited singlet energy S1 (G1) of the first sensitizing material and the energy gap T77K (G1) at 77 [K] of the first sensitizing material satisfies the mathematical formula (number 1): [Delta] ST (G1) = S1 (G1)-T77K (G1) lt; 0.5 eV... (number 1).

Description

Technical Field

[0001] This invention relates to organic electroluminescent elements, organic electroluminescent devices, electronic devices, light emitters, solar cells, and light sensors. Background Technology

[0002] Upconversion, a technology that converts low-energy light into high-energy light, has attracted attention.

[0003] Upconversion has attracted attention as a technology that can be driven at energies lower than those of emitted photons.

[0004] When upconversion technology is applied to photoexcitation, it is possible to obtain excitation light with a wavelength longer than that emitted.

[0005] For example, it is known that in upconversion using inorganic compounds, visible light can be generated from infrared light by using multi-level excitation of the ff transition of rare earth ions.

[0006] Furthermore, it is known that in optical upconversion using organic materials, short-wavelength light can actually be obtained from long-wavelength light through the interaction between multiple excited states (e.g., Triplet-Triplet Fusion = TTF).

[0007] On the other hand, it is anticipated that by applying upconversion techniques to electrical excitation, luminescence can be achieved with energy lower than the luminescence energy (in electron volts (eV)), i.e., with a lower applied voltage. That is, luminescence at a low applied voltage means that the driving voltage can be reduced.

[0008] In organic electroluminescent devices (sometimes called organic EL devices), fluorescent element materials achieve high efficiency by inducing TTF in the bulk of the luminescent layer, converting the excited triplet state to the excited singlet state, and then reusing the energy as light emission through energy transfer to the dopant (e.g., Patent Document 1). This is one type of upconversion luminescence in organic solid films.

[0009] For example, Non-Patent Document 1 describes the introduction of a phosphorescent complex (PtOEP) as an upconversion element of a sensitizing material into a multilayer structure composed of an organic solid film.

[0010] Existing technical documents

[0011] Patent documents

[0012] Patent Document 1: International Publication No. 2010 / 134350

[0013] Non-patent literature

[0014] Non-patent literature 1: Ting-An Lin et al., ADVANCED MATERIALS COMMUNICATION, 2020, 32, 1908-175 Summary of the Invention

[0015] The technical problem that the invention aims to solve

[0016] However, in the upconversion element of Non-Patent Document 1, although there is a possibility of low voltage due to the low external quantum efficiency (EQE) (around 0.024%), it is not expected to achieve low power consumption. This is because, since phosphorescent complexes can cause concentration quenching, the phosphorescent complexes cannot function effectively in the light-emitting layer (solid film) of the organic EL element when they are introduced into it.

[0017] In recent years, the demand for further high performance of organic EL components has led to requirements for low power consumption, such as extending battery life in mobile devices.

[0018] There is an urgent need for organic EL devices that efficiently incorporate upconversion in the emitting layer and are driven by low power consumption.

[0019] The purpose of this invention is to provide an organic electroluminescent element, an organic electroluminescent device, and an electronic device equipped with the organic electroluminescent element or the organic electroluminescent device that emits light with low light-emitting start voltage and high efficiency.

[0020] Another object of the present invention is to provide a light emitter with a low light emission initiation voltage and high light emission efficiency, as well as a solar cell and a light sensor equipped with the light emitter.

[0021] Solution to the above technical problems

[0022] According to one aspect of the present invention, an organic electroluminescent element is provided, comprising an anode, a cathode, and a light-emitting region disposed between the anode and the cathode. The light-emitting region includes a first sensitization layer and a first light-emitting layer. The first sensitization layer contains a first host material and a first sensitizing material, and the first light-emitting layer contains a second host material and a first luminescent compound. The first host material and the second host material are different from each other, and the first sensitizing material and the first luminescent compound are different from each other. The lowest excitation singlet energy S1(G1) of the first sensitizing material is different from the band gap T at 77 K of the first sensitizing material. 77K The difference ΔST(G1) between G1 and G1 satisfies the following mathematical expression (number 1).

[0023] ΔST(G1)=S1(G1)-T 77K (G1)<0.5eV…(Number 1)

[0024] According to one aspect of the present invention, an organic electroluminescent device is provided, comprising the organic electroluminescent element and a power source of the present invention described above, wherein the power source comprises a power generation element that generates a potential difference or current through external stimulation.

[0025] According to one aspect of the present invention, an electronic device may be provided, which is equipped with the organic electroluminescent element or the organic electroluminescent device of the present invention described above.

[0026] According to one aspect of the present invention, a light emitter is provided, comprising a first sensitization portion and a first light-emitting portion. The first sensitization portion contains a first host material and a first sensitizing material, and the first light-emitting portion contains a second host material and a first luminescent compound. The first host material and the second host material are different from each other, and the first sensitizing material and the first luminescent compound are different from each other. The lowest excitation singlet state energy S1(G1) of the first sensitizing material is different from the band gap T of the first sensitizing material at 77 [K]. 77K The difference ΔST(G1) between the first sensitized material and the second sensitized material at 77K satisfies the following mathematical expression (Form 1). 77K (G1), the band gap T of the first host material at 77K. 77K (H1), and the band gap T at 77 [K] of the second host material. 77K (H2) satisfies the following mathematical expression (Number 2), and the lowest excitation singlet state energy S1(G1) of the first sensitized material and the lowest excitation singlet state energy S1(BD1) of the first luminescent compound satisfy the following mathematical expression (Number 3).

[0027] ΔST(G1)=S1(G1)-T 77K (G1)<0.5eV…(Number 1)

[0028] T 77K (G1)>T 77K (H1)>T 77K (H2)…(Number 2)

[0029] S1(BD1)>S1(G1)…(Number 3)

[0030] According to one aspect of the present invention, a solar cell equipped with a light-emitting element according to one aspect of the present invention can be provided.

[0031] According to one aspect of the present invention, a light sensor equipped with a light-emitting element according to one aspect of the present invention can be provided.

[0032] According to one aspect of the present invention, it is possible to provide an organic electroluminescent element with low light emission initiation voltage and high light emission efficiency, an organic electroluminescent device, and an electronic device equipped with the organic electroluminescent element or the organic electroluminescent device.

[0033] According to another aspect of the present invention, it is possible to provide a light emitter with a low light emission initiation voltage and high light emission efficiency, as well as a solar cell and a light sensor equipped with the light emitter. Attached Figure Description

[0034] Figure 1 This is a diagram used to illustrate the light-emitting mechanism of the stacked light-emitting layer in the first embodiment.

[0035] Figure 2A This diagram illustrates the luminescence mechanism of a fluorescent luminescent layer (monolayer).

[0036] Figure 2B This diagram illustrates the light emission mechanism of a stacked light-emitting layer containing a Pt complex.

[0037] Figure 3 This is a diagram showing a schematic configuration of an example of an organic EL element according to the first embodiment.

[0038] Figure 4 This is a diagram showing a schematic configuration of another example of the organic EL element of the first embodiment.

[0039] Figure 5 This is a schematic diagram of a device for measuring transient pulse (PL).

[0040] Figure 6 This is a graph showing an example of the decay curve of the transition PL.

[0041] Figure 7 This is a diagram showing the measurement system for the transition EL waveform.

[0042] Figure 8A The graph shows the method for measuring the luminescence intensity ratio derived from delayed fluorescence, and the chart shows the time variation of the luminescence intensity of the organic EL elements of Examples 1-2 and Comparative Example 1.

[0043] Figure 8B The graph shows the method for measuring the ratio of luminous intensity derived from delayed fluorescence, and the chart shows the time variation of the reciprocal of the square root of the light intensity of the organic EL elements of Examples 1-2 and Comparative Example 1.

[0044] Figure 9 This is a diagram showing a schematic configuration of an example of an organic EL element according to the second embodiment.

[0045] Figure 10This is a diagram illustrating a schematic configuration of another example of the organic EL element according to the second embodiment.

[0046] Figure 11 This is a diagram illustrating a schematic configuration of another example of the organic EL element according to the second embodiment.

[0047] Figure 12 This is a diagram showing a schematic configuration of an example of an organic EL device according to the third embodiment.

[0048] Figure 13A This is a diagram showing a schematic configuration of an example of the light-emitting body according to the fifth embodiment.

[0049] Figure 13B This is a diagram showing a schematic configuration of another example of the light-emitting body according to the fifth embodiment.

[0050] Figure 14A The spectroscopic emission brightness spectra of the organic EL elements of Examples 1-2 and Comparative Example 1 are measured when the element is energized with a voltage of 2.40V.

[0051] Figure 14B The spectroscopic emission brightness spectra of the organic EL elements of Examples 1-2 and Comparative Example 1 are measured when the element is powered on at a voltage of 2.45V. Detailed Implementation

[0052] [definition]

[0053] In this specification, hydrogen atoms include isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0054] In this specification, it is assumed that hydrogen atoms are bonded at the bonding positions of symbols such as "R" or "D" representing deuterium atoms in the chemical structural formula, that is, protium atoms, deuterium atoms, or tritium atoms are bonded.

[0055] In this specification, the number of carbon atoms forming a ring refers to the number of carbon atoms in the atoms constituting the ring itself in a compound with a cyclic structure formed by atomic bonds (e.g., monocyclic compounds, fused-ring compounds, cross-linked compounds, carbocyclic compounds, and heterocyclic compounds). When the ring is substituted with a substituent, the carbon atoms contained in the substituent are not included in the number of carbon atoms forming the ring. This also applies to the "number of carbon atoms forming a ring" described below unless otherwise specified. For example, the number of carbon atoms forming a ring is 6 for a benzene ring, 10 for a naphthalene ring, 5 for a pyridine ring, and 4 for a furan ring. Furthermore, for example, the number of carbon atoms forming a ring is 13 for 9,9-diphenylfluoreneyl and 25 for 9,9'-spirodifluoreneyl.

[0056] Furthermore, when the benzene ring is substituted with an alkyl group, the number of carbon atoms in that alkyl group is not included in the total number of carbon atoms in the cyclic ring of the benzene ring. Therefore, the benzene ring substituted with an alkyl group has a total of 6 carbon atoms. Similarly, when the naphthalene ring is substituted with an alkyl group, the number of carbon atoms in that alkyl group is not included in the total number of carbon atoms in the cyclic ring of the naphthalene ring. Therefore, the naphthalene ring substituted with an alkyl group has a total of 10 carbon atoms.

[0057] In this specification, the number of cyclic atoms refers to the number of atoms constituting the ring itself in compounds (e.g., monocyclic compounds, fused-ring compounds, cross-linked compounds, carbocyclic compounds, and heterocyclic compounds) that form a cyclic structure (e.g., monocyclic, fused-ring, and aggregated rings) by atomic bonds. Atoms that do not constitute a ring (e.g., hydrogen atoms terminating the bonds between the ring-forming atoms) and atoms contained in substituents when the ring is substituted are not included in the number of cyclic atoms. This also applies to the "number of cyclic atoms" described below unless otherwise specified. For example, the number of cyclic atoms in a pyridine ring is 6, in a quinazoline ring it is 10, and in a furan ring it is 5. For example, the number of hydrogen atoms bonded to the pyridine ring or atoms constituting substituents are not included in the number of cyclic atoms in the pyridine ring. Therefore, the number of cyclic atoms in a pyridine ring bonded with hydrogen atoms or substituents is 6. Furthermore, for example, hydrogen atoms bonded to the carbon atoms of the quinazoline ring, or atoms constituting substituents, are not included in the number of cyclic atoms of the quinazoline ring. Therefore, the number of cyclic atoms in a quinazoline ring bonded to hydrogen atoms or substituents is 10.

[0058] In this specification, the phrase "a ZZ group with XX to YY carbons, whether substituted or unsubstituted" refers to the number of carbons in the case where the ZZ group is unsubstituted, and the number of carbons in the case where there is no substitution. Here, "YY" is greater than "XX", where "XX" represents an integer greater than 1, and "YY" represents an integer greater than 2.

[0059] In this specification, the phrase "ZZ group with XX to YY atoms of substituted or unsubstituted atoms" refers to the number of atoms in the ZZ group when it is unsubstituted, and the number of atoms in the substituent group when it is unsubstituted. Here, "YY" is greater than "XX", where "XX" represents an integer greater than 1 and "YY" represents an integer greater than 2.

[0060] In this specification, "unsubstituted ZZ group" means "unsubstituted ZZ group" and "substituted ZZ group" means "substituted ZZ group".

[0061] In this specification, "unsubstituted" in the case of "substituted or unsubstituted ZZ group" means that the hydrogen atom in the ZZ group is not substituted as a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom, or a tritium atom.

[0062] Furthermore, in this specification, "substitution" in the case of "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced by substituents. Similarly, "substitution" in the case of "BB group substituted by AA group" also means that one or more hydrogen atoms in the BB group are replaced by AA group.

[0063] Substituents described in this specification

[0064] The substituents described in this specification are explained below.

[0065] Unless otherwise specified in this specification, the number of carbon atoms in the cyclic group of "unsubstituted aryl" as described in this specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0066] Unless otherwise specified in this specification, the number of cyclic atoms in the "unsubstituted heterocyclic group" described in this specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.

[0067] Unless otherwise specified in this specification, the number of carbon atoms in "unsubstituted alkyl" as described in this specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0068] Unless otherwise specified in this specification, the number of carbons in the "unsubstituted alkenyl group" described in this specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.

[0069] Unless otherwise specified in this specification, the number of carbons in the "unsubstituted alkynyl group" described in this specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.

[0070] Unless otherwise specified in this specification, the number of carbon atoms in the cyclic structure of "unsubstituted cycloalkyl" as described in this specification is 3 to 50, preferably 3 to 20, and more preferably 3 to 6.

[0071] Unless otherwise specified in this specification, the number of carbon atoms in the cyclic formation of the "unsubstituted aryl group" described in this specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0072] Unless otherwise specified in this specification, the number of cyclic atoms in the "unsubstituted divalent heterocyclic group" described in this specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.

[0073] Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted alkylene" described in this specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0074] • "Substituted or unsubstituted aryl groups"

[0075] As specific examples (specific example group G1) of "substituted or unsubstituted aryl" described in this specification, the following examples include unsubstituted aryl (specific example group G1A) and substituted aryl (specific example group G1B). (Here, unsubstituted aryl refers to the case where "substituted or unsubstituted aryl" is "unsubstituted aryl", and substituted aryl refers to the case where "substituted or unsubstituted aryl" is "substituted aryl".) In this specification, the term "aryl" includes both "unsubstituted aryl" and "substituted aryl".

[0076] "Substituted aryl" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl" are replaced by substituents. Examples of "substituted aryl" include the group in Specific Example Group G1A below, in which one or more hydrogen atoms of an "unsubstituted aryl" are replaced by substituents, and the substituted aryl group in Specific Example Group G1B below. Furthermore, the examples of "unsubstituted aryl" and "substituted aryl" given here are only examples; the "substituted aryl" described in this specification also includes: groups in which hydrogen atoms bonded to the carbon atoms of the aryl group itself in the "substituted aryl" of Specific Example Group G1B below are further replaced by substituents, and groups in which hydrogen atoms of the substituents in the "substituted aryl" of Specific Example Group G1B below are further replaced by substituents.

[0077] • Unsubstituted aryl groups (specific example group G1A):

[0078] phenyl,

[0079] p-phenyl,

[0080] metaphenyl,

[0081] o-phenyl,

[0082] p-Triphenyl-4-yl,

[0083] p-Triphenyl-3-yl,

[0084] p-Triphenyl-2-yl,

[0085] Meta-triphenyl-4-yl,

[0086] Meta-triphenyl-3-yl,

[0087] Meta-triphenyl-2-yl,

[0088] o-Triphenyl-4-yl,

[0089] o-Triphenyl-3-yl,

[0090] o-Triphenyl-2-yl,

[0091] 1-Naphthyl,

[0092] 2-Naphthyl,

[0093] anthracene,

[0094] Benzanthracene,

[0095] Fiki,

[0096] Benzphenanthrene,

[0097] Finadenyl,

[0098] Pyrene

[0099] base,

[0100] benzo[a] base,

[0101] Tri-phenylene,

[0102] Benzotrimethylene

[0103] Tetracenyl

[0104] Pentaphenyl

[0105] Fluorine

[0106] 9,9'-spirodifluorene,

[0107] benzo[f]fluorenyl,

[0108] Dibenzofluorene,

[0109] Fluoranthene group,

[0110] Benzofluoranthyl,

[0111] Perylene, and

[0112] A monovalent aryl group is derived by removing one hydrogen atom from a ring structure represented by the following general formulas (TEMP-1) to (TEMP-15).

[0113] [Chemistry 1]

[0114]

[0115] [Chemistry 2]

[0116]

[0117] • Substituted aryl groups (specific example group G1B):

[0118] o-Tolyl,

[0119] m-Tolyl,

[0120] p-Tolyl,

[0121] p-Xylyl,

[0122] m-Xylyl,

[0123] o-xylyl,

[0124] p-isopropylphenyl,

[0125] m-Isopropylphenyl,

[0126] o-isopropylphenyl,

[0127] p-tert-butylphenyl,

[0128] m-tert-butylphenyl,

[0129] o-tert-butylphenyl,

[0130] 3,4,5-Trimethylphenyl,

[0131] 9,9-Dimethylfluorenyl,

[0132] 9,9-Diphenylfluorenyl,

[0133] 9,9-bis(4-methylphenyl)fluorenyl,

[0134] 9,9-Bis(4-isopropylphenyl)fluorenyl,

[0135] 9,9-Bis(4-tert-butylphenyl)fluorenyl,

[0136] Cyanophenyl,

[0137] Triphenylsilylphenyl

[0138] Trimethylsilylphenyl

[0139] Benzonaphthyl,

[0140] Naphthalenephenyl, and

[0141] A group obtained by replacing one or more hydrogen atoms of a monovalent group derived from a ring structure represented by the general formula (TEMP-1) to (TEMP-15) with substituents.

[0142] • "Substituted or unsubstituted heterocyclic groups"

[0143] The term "heterocyclic group" as used in this specification refers to a cyclic group containing at least one heteroatom in its cyclic atom. Specific examples of heteroatoms include nitrogen, oxygen, sulfur, silicon, phosphorus, and boron atoms.

[0144] The term "heterocyclic group" as used in this specification refers to a monocyclic group or a fused-ring group.

[0145] The term "heterocyclic group" as used in this specification refers to either an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0146] As specific examples of "substituted or unsubstituted heterocyclic groups" described in this specification (specific example group G2), the following unsubstituted heterocyclic groups (specific example group G2A) and substituted heterocyclic groups (specific example group G2B) are examples. (Here, an unsubstituted heterocyclic group refers to the case where "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group," and a substituted heterocyclic group refers to the case where "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group.") In this specification, the term "heterocyclic group" includes both "unsubstituted heterocyclic group" and "substituted heterocyclic group."

[0147] "Substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced by substituents. Specific examples of "substituted heterocyclic groups" include the group in Example Group G2A below, in which hydrogen atoms of the "unsubstituted heterocyclic group" are replaced, and the examples of substituted heterocyclic groups in Example Group G2B below. In addition, the examples of "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" given here are only examples. The "substituted heterocyclic groups" described in this specification also include: groups in which hydrogen atoms bonded to the cyclic atoms of the heterocyclic group itself in the "substituted heterocyclic group" of Example Group G2B are further replaced by substituents, and groups in which hydrogen atoms of the substituents in the "substituted heterocyclic group" of Example Group G2B are further replaced by substituents.

[0148] Specific example group G2A includes, for example, the following groups: unsubstituted heterocyclic groups containing nitrogen atoms (specific example group G2A1), unsubstituted heterocyclic groups containing oxygen atoms (specific example group G2A2), unsubstituted heterocyclic groups containing sulfur atoms (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4).

[0149] Specific example group G2B includes, for example, the following groups: a heterocyclic group containing a nitrogen atom (specific example group G2B1), a heterocyclic group containing an oxygen atom (specific example group G2B2), a heterocyclic group containing a sulfur atom (specific example group G2B3), and a group obtained by substituting one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) as substituents (specific example group G2B4).

[0150] • Unsubstituted heterocyclic groups containing nitrogen atoms (specific example group G2A1):

[0151] pyrrole,

[0152] Imidazole group,

[0153] Pyrazolyl,

[0154] Triazole group,

[0155] Tetrazolyl,

[0156] Oxazolyl,

[0157] Isoxazolyl,

[0158] Oxadiazole group,

[0159] Thiazole group,

[0160] Isothiazolyl,

[0161] Thiadiazole group,

[0162] pyridyl,

[0163] pyridazinyl,

[0164] Pyrimidinyl,

[0165] Pyrazinyl,

[0166] Triazine group

[0167] Indole,

[0168] Isoindolyl,

[0169] Indoleazine,

[0170] Quinazine-based

[0171] Quinoline,

[0172] Isoquinoline,

[0173] cinnolyl group

[0174] Phthaloazine

[0175] Quinazolinyl,

[0176] Quinoxaloyl,

[0177] Benzimidazole group,

[0178] Indazole group,

[0179] phenanthroline,

[0180] phenanthridine,

[0181] acridine group,

[0182] Phenazine group,

[0183] Carbazolyl,

[0184] Benzocarbazolyl,

[0185] Morpholinyl

[0186] phenoxazine group,

[0187] phenothiazine group,

[0188] Azacarbazolyl and diazacarbazolyl.

[0189] • Unsubstituted heterocyclic groups containing oxygen atoms (specific example group G2A2):

[0190] furanyl,

[0191] Oxazolyl,

[0192] Isoxazolyl,

[0193] Oxadiazole group,

[0194] Xuton base,

[0195] Benzofuranyl,

[0196] Isobenzofuranyl,

[0197] Dibenzofuranyl,

[0198] Naphthobenzofuranyl,

[0199] Benzoxazolyl,

[0200] Benzisoxazole group,

[0201] phenoxazine group,

[0202] Morpholinyl

[0203] Dinaphthylfuranyl,

[0204] Azadibenzofuranyl,

[0205] diazadibenzofuranyl,

[0206] Azanaphthalenebenzofuranyl, and

[0207] Diazanaphthenebenzofuranyl.

[0208] • Unsubstituted heterocyclic groups containing sulfur atoms (specific example group G2A3):

[0209] Thiophene group

[0210] Thiazole group,

[0211] Isothiazolyl,

[0212] Thiadiazole group,

[0213] benzothienyl group

[0214] isobenzothienyl group

[0215] dibenzothienyl group

[0216] Naphthobenzothienyl group

[0217] Benzothiazolyl,

[0218] Benzisothiazolyl,

[0219] phenothiazine group,

[0220] dinaphthothienyl group

[0221] Azadibenzothienyl group

[0222] diazadibenzothienyl group

[0223] azanaphthobenzothienyl group, and

[0224] diazanaphthobenzothienyl group.

[0225] • Monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structures represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4):

[0226] [Chemistry 3]

[0227]

[0228] [Chemistry 4]

[0229]

[0230] In the general formulas (TEMP-16) to (TEMP-33), X A and Y A Each can be independently represented by an oxygen atom, a sulfur atom, NH, or CH2. Where X... A and Y A At least one of them is an oxygen atom, a sulfur atom, or NH.

[0231] In the general formulas (TEMP-16) to (TEMP-33), in X A and Y A When at least one of them is NH or CH2, the monovalent heterocyclic group derived from the ring structure represented by the general formula (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.

[0232] • Heterocyclic groups containing nitrogen atoms (specific example group G2B1):

[0233] (9-phenyl)carbazole group,

[0234] (9-Biphenyl)carbazolyl,

[0235] (9-Phenyl)phenylcarbazolyl,

[0236] (9-Naphthyl)carbazole,

[0237] Diphenylcarbazole-9-yl,

[0238] Phenylexacarbazole-9-yl,

[0239] Methylbenzimidazole,

[0240] Ethylbenzimidazole,

[0241] Phenylacetyl,

[0242] Biphenyltriazine

[0243] diphenyltriazine group,

[0244] Phenylacetyl and biphenylquinazolinyl.

[0245] • Heterocyclic groups containing oxygen atoms (specific example group G2B2):

[0246] Phenyl dibenzofuranyl,

[0247] Methyldibenzofuranyl,

[0248] tert-butyldibenzofuranyl, and

[0249] The monovalent residues of [9H-xanton-9,9'-[9H]fluorene].

[0250] • Heterocyclic groups containing sulfur atoms (specific example group G2B3):

[0251] Phenyl dibenzothiophene,

[0252] Methyldibenzothiophene,

[0253] tert-butyldibenzothiophene, and

[0254] The monovalent residue of [9H-thioxanth-9,9'-[9H]fluorene].

[0255] • A group obtained by substituting one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the general formulas (TEMP-16) to (TEMP-33) as substituents (specific example group G2B4):

[0256] The phrase "one or more hydrogen atoms of a monovalent heterocyclic group" refers to one or more hydrogen atoms selected from the hydrogen atoms bonded to the cyclic carbon atom of the monovalent heterocyclic group, the hydrogen atoms bonded to the nitrogen atom when at least one of XA and YA is NH, and the hydrogen atoms of the methylene group when one of XA and YA is CH2.

[0257] • "Substituted or unsubstituted alkyl groups"

[0258] As specific examples of "substituted or unsubstituted alkyl" described in this specification (specific example group G3), the following unsubstituted alkyl (specific example group G3A) and substituted alkyl (specific example group G3B) can be cited. (Here, unsubstituted alkyl refers to the case where "substituted or unsubstituted alkyl" is "unsubstituted alkyl", and substituted alkyl refers to the case where "substituted or unsubstituted alkyl" is "substituted alkyl".) Hereinafter, when simply referred to as "alkyl", both "unsubstituted alkyl" and "substituted alkyl" are included.

[0259] "Substituted alkyl" refers to a group obtained by replacing one or more hydrogen atoms in an "unsubstituted alkyl" group with substituents. Specific examples of "substituted alkyl" include groups obtained by replacing one or more hydrogen atoms in an "unsubstituted alkyl" group (specific example group G3A) with substituents, and examples of substituted alkyl groups (specific example group G3B). In this specification, "unsubstituted alkyl" refers to a chain alkyl group. Therefore, "unsubstituted alkyl" includes both straight-chain and branched-chain "unsubstituted alkyl". Furthermore, the examples of "unsubstituted alkyl" and "substituted alkyl" given here are only examples; the "substituted alkyl" described in this specification also includes groups obtained by further replacing the hydrogen atoms of the alkyl group itself in a "substituted alkyl" group of specific example group G3B with substituents, and groups obtained by further replacing the hydrogen atoms of the substituents in a "substituted alkyl" group of specific example group G3B with substituents.

[0260] • Unsubstituted alkyl groups (specific example group G3A):

[0261] methyl,

[0262] Ethyl,

[0263] n-propyl,

[0264] Isopropyl,

[0265] n-Butyl,

[0266] Isobutyl,

[0267] sec-butyl, and

[0268] tert-butyl.

[0269] • Substituted alkyl groups (specific example group G3B):

[0270] Heptafluoropropyl (including isomers),

[0271] Pentafluoroethyl,

[0272] 2,2,2-Trifluoroethyl, and

[0273] Trifluoromethyl

[0274] • "Substituted or unsubstituted alkenyl groups"

[0275] As specific examples of "substituted or unsubstituted alkenyl groups" described in this specification (specific example group G4), the following examples include unsubstituted alkenyl groups (specific example group G4A) and substituted alkenyl groups (specific example group G4B), etc. (Here, "unsubstituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is "unsubstituted alkenyl group", and "substituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is "substituted alkenyl group".) In this specification, when simply referred to as "alkenyl group", both "unsubstituted alkenyl group" and "substituted alkenyl group" are included.

[0276] "Substituted alkenyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl" are replaced by substituents. Specific examples of "substituted alkenyl" include the substituent group of the "unsubstituted alkenyl" (specific example group G4A) described below, and examples of substituted alkenyl (specific example group G4B). Furthermore, the examples of "unsubstituted alkenyl" and "substituted alkenyl" given here are only examples; the "substituted alkenyl" described in this specification also includes: groups in which the hydrogen atoms of the alkenyl itself in the "substituted alkenyl" of specific example group G4B are further replaced by substituents, and groups in which the hydrogen atoms of the substituents in the "substituted alkenyl" of specific example group G4B are further replaced by substituents.

[0277] • Unsubstituted alkenyl groups (specific example group G4A):

[0278] vinyl,

[0279] Allyl

[0280] 1-Butenyl,

[0281] 2-Butenyl, and

[0282] 3-Butenyl.

[0283] • Substituted alkenyl groups (specific example group G4B):

[0284] 1,3-Butadienyl,

[0285] 1-Methylvinyl

[0286] 1-Methylallyl,

[0287] 1,1-Dimethylallyl,

[0288] 2-Methylallyl, and

[0289] 1,2-Dimethylallyl.

[0290] • "Substituted or unsubstituted alkynyl groups"

[0291] As specific examples of "substituted or unsubstituted alkynyl groups" described in this specification (specific example group G5), the following unsubstituted alkynyl groups (specific example group G5A) are examples. (Here, unsubstituted alkynyl group refers to the case where "substituted or unsubstituted alkynyl group" is "unsubstituted alkynyl group".) Hereinafter, when simply referred to as "alkynyl group", it includes both "unsubstituted alkynyl group" and "substituted alkynyl group".

[0292] "Substituted alkynyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl" are replaced by substituents. Specific examples of "substituted alkynyl" include groups in which one or more hydrogen atoms in an "unsubstituted alkynyl" (specific example group G5A) are replaced by substituents.

[0293] • Unsubstituted alkynyl group (specific example group G5A):

[0294] Acetylene group.

[0295] • "Substituted or unsubstituted cycloalkyl groups"

[0296] As specific examples of "substituted or unsubstituted cycloalkyl" described in this specification (specific example group G6), the following examples include unsubstituted cycloalkyl (specific example group G6A) and substituted cycloalkyl (specific example group G6B). (Here, unsubstituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "unsubstituted cycloalkyl", and substituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "substituted cycloalkyl".) In this specification, the term "cycloalkyl" includes both "unsubstituted cycloalkyl" and "substituted cycloalkyl".

[0297] "Substituted cycloalkyl" refers to a group obtained by replacing one or more hydrogen atoms in an "unsubstituted cycloalkyl" group with substituents. Specific examples of "substituted cycloalkyl" include groups obtained by replacing one or more hydrogen atoms in an "unsubstituted cycloalkyl" group (specific example group G6A) with substituents, and examples of substituted cycloalkyl groups (specific example group G6B). Furthermore, the examples of "unsubstituted cycloalkyl" and "substituted cycloalkyl" given here are only examples; the "substituted cycloalkyl" described in this specification also includes groups obtained by replacing one or more hydrogen atoms bonded to the carbon atom of the cycloalkyl group itself in the "substituted cycloalkyl" group of specific example group G6B with substituents, and groups obtained by further replacing the hydrogen atoms of the substituents in the "substituted cycloalkyl" group of specific example group G6B with substituents.

[0298] • Unsubstituted cycloalkyl groups (specific example group G6A):

[0299] Cyclopropyl

[0300] Cyclobutyl,

[0301] Cyclopentyl,

[0302] Cyclohexyl,

[0303] 1-Adamantyl,

[0304] 2-Adamantyl,

[0305] 1-norborneol, and

[0306] 2-norborneol.

[0307] • Substituted cycloalkyl groups (specific example group G6B):

[0308] 4-Methylcyclohexyl.

[0309] • "with-Si(R) 901 (R) 902 (R) 903 (represented by a group)

[0310] As described in this specification, -Si(R) 901 (R) 902 (R) 903 Specific examples of the group represented by ) (specific example group G7) can be given as follows:

[0311] -Si(G1)(G1)(G1),

[0312] -Si(G1)(G2)(G2)

[0313] -Si(G1)(G1)(G2),

[0314] -Si(G2)(G2)(G2),

[0315] -Si(G3)(G3)(G3), and

[0316] -Si(G6)(G6)(G6).

[0317] Here,

[0318] G1 is the “substituted or unsubstituted aryl group” recorded in the specific example group G1.

[0319] G2 is the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0320] G3 is the “substituted or unsubstituted alkyl group” described in the specific example group G3.

[0321] G6 is "substituted or unsubstituted cycloalkyl" as described in specific example group G6.

[0322] In -Si(G1)(G1)(G1), multiple G1s may be the same or different from each other.

[0323] In -Si(G1)(G2)(G2), multiple G2s may be the same or different from each other.

[0324] In -Si(G1)(G1)(G2), multiple G1s may be the same or different from each other.

[0325] In -Si(G2)(G2)(G2), multiple G2s may be the same or different from each other.

[0326] In -Si(G3)(G3)(G3), multiple G3s may be the same or different from each other.

[0327] In -Si(G6)(G6)(G6), multiple G6s may be the same or different from each other.

[0328] ·“with-O-(R 904 (represented by a group)

[0329] As described in this specification, -O-(R) 904 Specific examples of the group represented by ) (specific example group G8) can be given as follows:

[0330] -O(G1)

[0331] -O(G2),

[0332] -O(G3), and

[0333] -O(G6).

[0334] Here,

[0335] G1 is the “substituted or unsubstituted aryl group” recorded in the specific example group G1.

[0336] G2 is the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0337] G3 is the “substituted or unsubstituted alkyl group” described in the specific example group G3.

[0338] G6 is "substituted or unsubstituted cycloalkyl" as described in specific example group G6.

[0339] ·“with-S-(R 905 (represented by a group)

[0340] As described in this specification, -S-(R) 905 Specific examples of the group represented by ) (specific example group G9) can be given as follows:

[0341] -S(G1)

[0342] -S(G2),

[0343] -S(G3), and

[0344] -S(G6).

[0345] Here,

[0346] G1 is the “substituted or unsubstituted aryl group” recorded in the specific example group G1.

[0347] G2 is the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0348] G3 is the “substituted or unsubstituted alkyl group” described in the specific example group G3.

[0349] G6 is "substituted or unsubstituted cycloalkyl" as described in specific example group G6.

[0350] • "with -N(R 906 (R) 907 (represented by a group)

[0351] As described in this specification, -N(R) 906 (R) 907 Specific examples of the group represented by ) (specific example group G10) can be given as follows:

[0352] -N(G1)(G1),

[0353] -N(G2)(G2),

[0354] -N(G1)(G2),

[0355] -N(G3)(G3), and

[0356] -N(G6)(G6).

[0357] Here,

[0358] G1 is the “substituted or unsubstituted aryl group” recorded in the specific example group G1.

[0359] G2 is the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0360] G3 is the “substituted or unsubstituted alkyl group” described in the specific example group G3.

[0361] G6 is "substituted or unsubstituted cycloalkyl" as described in specific example group G6.

[0362] In -N(G1)(G1), multiple G1s may be the same or different from each other.

[0363] In -N(G2)(G2), multiple G2s may be the same or different from each other.

[0364] In -N(G3)(G3), multiple G3s may be the same or different from each other.

[0365] In -N(G6)(G6), multiple G6s may be the same or different from each other.

[0366] • "Halogen atom"

[0367] Specific examples of "halogen atoms" described in this specification (specific example group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0368] • "Substituted or unsubstituted fluoroalkyl groups"

[0369] The term "substituted or unsubstituted fluoroalkyl" as used in this specification refers to a group obtained by replacing at least one hydrogen atom bonded to the carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl" with a fluorine atom, and also includes a group obtained by replacing all hydrogen atoms bonded to the carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl" with fluorine atoms (perfluoroalkyl). Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted fluoroalkyl" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. "Substituted fluoroalkyl" refers to a group obtained by replacing one or more hydrogen atoms of the "fluoroalkyl" with a substituent. In addition, the term "substituted fluoroalkyl" as used in this specification also includes: a group obtained by further replacing one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in the "substituted fluoroalkyl" with a substituent, and a group obtained by further replacing one or more hydrogen atoms of the substituent in the "substituted fluoroalkyl" with a substituent. As a specific example of "unsubstituted fluoroalkyl", examples can be given of groups in which one or more hydrogen atoms in the "alkyl" (specific example group G3) are replaced with fluorine atoms.

[0370] • "Substituted or unsubstituted haloalkyl groups"

[0371] The term "substituted or unsubstituted haloalkyl" as used in this specification refers to a group obtained by replacing at least one hydrogen atom bonded to the carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl" with a halogen atom, and also includes a group obtained by replacing all hydrogen atoms bonded to the carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl" with halogen atoms. Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted haloalkyl" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. "Substituted haloalkyl" refers to a group obtained by replacing one or more hydrogen atoms in the "haloalkyl" with a substituent. In addition, the term "substituted haloalkyl" as used in this specification also includes: a group obtained by further replacing one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in the "substituted haloalkyl" with a substituent, and a group obtained by further replacing one or more hydrogen atoms of the substituent in the "substituted haloalkyl". As a specific example of "unsubstituted haloalkyl", examples can be given of groups in which one or more hydrogen atoms in the "alkyl" (specific example group G3) are replaced with halogen atoms. Sometimes haloalkyl is referred to as alkyl halide.

[0372] • "Substituted or unsubstituted alkoxy groups"

[0373] As a specific example of "substituted or unsubstituted alkoxy group" as described in this specification, it is a group represented by -O (G3), where G3 refers to the "substituted or unsubstituted alkyl group" described in the specific example group G3. Unless otherwise specified in this specification, the "unsubstituted alkoxy group" has 1 to 50 carbon atoms, preferably 1 to 30, and more preferably 1 to 18.

[0374] • "Substituted or unsubstituted alkylthio groups"

[0375] As a specific example of "substituted or unsubstituted alkylthio group" as described in this specification, it is a group represented by -S(G3), where G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3. Unless otherwise specified in this specification, the "unsubstituted alkylthio group" has 1 to 50 carbon atoms, preferably 1 to 30, and more preferably 1 to 18.

[0376] • "Substituted or unsubstituted aryloxy groups"

[0377] As a specific example of "substituted or unsubstituted aryloxy group" as described in this specification, it is a group represented by -O (G1), where G1 refers to the "substituted or unsubstituted aryl group" described in specific example group G1. Unless otherwise specified in this specification, the number of carbon atoms in the cyclic group of "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0378] • "Substituted or unsubstituted arylthio groups"

[0379] As a specific example of "substituted or unsubstituted arylthio group" as described in this specification, it is a group represented by -S(G1), where G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1. Unless otherwise specified in this specification, the number of carbon atoms in the cyclic group of "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0380] • "Substituted or unsubstituted trialkylsilyl groups"

[0381] As a specific example of "trialkylsilyl" as described in this specification, it is a group represented by -Si(G3)(G3)(G3), where G3 refers to "substituted or unsubstituted alkyl" as described in the specific example group G3. The plurality of G3s in -Si(G3)(G3)(G3) may be the same or different from each other. Unless otherwise specified in this specification, the number of carbon atoms in each alkyl group of "trialkylsilyl" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0382] • "Substituted or unsubstituted aralkyl groups"

[0383] As a specific example of "substituted or unsubstituted aralkyl" as described in this specification, it is a group represented by -(G3)-(G1), where G3 refers to the "substituted or unsubstituted alkyl" described in specific example group G3, and G1 refers to the "substituted or unsubstituted aryl" described in specific example group G1. Therefore, "aralkyl" is a group obtained by replacing the hydrogen atom of "alkyl" with "aryl" as a substituent, and is a form of "substituted alkyl". "Unsubstituted aralkyl" is "unsubstituted alkyl" after "unsubstituted aryl" is substituted. Unless otherwise specified in this specification, the number of carbon atoms in "unsubstituted aralkyl" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18.

[0384] Specific examples of "substituted or unsubstituted aralkyl groups" include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, and 2-β-naphthylisopropyl.

[0385] Unless otherwise specified in this specification, the substituted or unsubstituted aryl groups described herein are preferably phenyl, p-phenyl, meta-phenyl, o-phenyl, p-triphenyl-4-yl, p-triphenyl-3-yl, p-triphenyl-2-yl, meta-triphenyl-4-yl, meta-triphenyl-3-yl, meta-triphenyl-2-yl, o-triphenyl-4-yl, o-triphenyl-3-yl, o-triphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthraceneyl, phenanthryl, pyreneyl, etc. It includes methyl, triphenyl, fluorenyl, 9,9'-spirodifluorenyl, 9,9-dimethylfluorenyl and 9,9-diphenylfluorenyl, etc.

[0386] Unless otherwise specified in this specification, the substituted or unsubstituted heterocyclic groups described herein are preferably pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, benzimidazolyl, phenanthrolinel, carbazole (1-carbazole, 2-carbazole, 3-carbazole, 4-carbazole or 9-carbazole), benzocarbazole, azacarbazole, diazacarbazole, dibenzofuranyl, naphthobenzofuranyl, azadibenzofuranyl, diazadibenzofuranyl, dibenzothiophene, naphthalene Benzothiophene, azadibenzothiophene, diazadibenzothiophene, (9-phenyl)carbazoyl ((9-phenyl)carbazo-1-yl, (9-phenyl)carbazo-2-yl, (9-phenyl)carbazo-3-yl or (9-phenyl)carbazo-4-yl), (9-biphenyl)carbazoyl, (9-phenyl)phenylcarbazoyl, diphenylcarbazo-9-yl, phenylcarbazo-9-yl, phenyltriazinyl, biphenyltriazinyl, diphenyltriazinyl, phenyldibenzofuranyl and phenyldibenzothiophene, etc.

[0387] Unless otherwise specified in this specification, the carbazoyl group specifically refers to any of the following groups.

[0388] [Chemistry 5]

[0389]

[0390] Unless otherwise specified in this specification, (9-phenyl)carbazolyl specifically refers to any of the following groups.

[0391] [Chemistry 6]

[0392]

[0393] In the general formulas (TEMP-Cz1) to (TEMP-Cz9), * indicates the bonding position.

[0394] Unless otherwise specified in this specification, dibenzofuranyl and dibenzothiopheneyl are specifically any of the following groups.

[0395] [Chemistry 7]

[0396]

[0397] In the general formulas (TEMP-34) to (TEMP-41), * indicates the bonding position.

[0398] Unless otherwise specified in this specification, the substituted or unsubstituted alkyl groups described herein are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and tert-butyl, etc.

[0399] • "Substituted or unsubstituted aryl groups"

[0400] Unless otherwise specified, the "substituted or unsubstituted aryl group" described in this specification is a divalent group derived from the "substituted or unsubstituted aryl group" by removing one hydrogen atom from the aromatic ring. Specific examples of "substituted or unsubstituted aryl group" (specific example group G12) include divalent groups derived from the "substituted or unsubstituted aryl group" described in specific example group G1 by removing one hydrogen atom from the aromatic ring.

[0401] • "Substituted or unsubstituted divalent heterocyclic group"

[0402] Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived from the "substituted or unsubstituted heterocyclic group" by removing one hydrogen atom from the heterocycle. As a specific example of the "substituted or unsubstituted divalent heterocyclic group" (specific example group G13), examples include divalent groups derived from the "substituted or unsubstituted heterocyclic group" described in specific example group G2 by removing one hydrogen atom from the heterocycle.

[0403] • "Substituted or unsubstituted alkylene compounds"

[0404] Unless otherwise specified, the term "substituted or unsubstituted alkylene" as used in this specification refers to a divalent group derived from the "substituted or unsubstituted alkyl" by removing one hydrogen atom from the alkyl chain. Specific examples of "substituted or unsubstituted alkylene" (specific example group G14) include divalent groups derived from the "substituted or unsubstituted alkyl" described in specific example group G3 by removing one hydrogen atom from the alkyl chain.

[0405] Unless otherwise specified in this specification, the substituted or unsubstituted aryl group described herein is preferably any one of the following general formulas (TEMP-42) to (TEMP-68).

[0406] [Chemistry 8]

[0407]

[0408] [Chemistry 9]

[0409]

[0410] In the general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 Each can be a hydrogen atom or a substituent, independently.

[0411] In the general formulas (TEMP-42) to (TEMP-52), * indicates the bonding position.

[0412] [Chemistry 10]

[0413]

[0414] In the general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each can be a hydrogen atom or a substituent, independently.

[0415] Formula Q9 and Q 10 They can form rings by bonding with each other through single bonds.

[0416] In the general formulas (TEMP-53) to (TEMP-62), * indicates the bonding position.

[0417] [Chemistry 11]

[0418]

[0419] In the general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0420] In the general formulas (TEMP-63) to (TEMP-68), * indicates the bonding position.

[0421] Unless otherwise specified in this specification, the substituted or unsubstituted divalent heterocyclic group described herein is preferably any one of the following general formulas (TEMP-69) to (TEMP-102).

[0422] [Chemistry 12]

[0423]

[0424] [Chemistry 13]

[0425]

[0426] [Chemistry 14]

[0427]

[0428] In the general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0429] [Chemistry 15]

[0430]

[0431] [Chemistry 16]

[0432]

[0433] [Chemistry 17]

[0434]

[0435] [Chemistry 18]

[0436]

[0437] In the general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0438] The above is an explanation of the substituents described in this specification.

[0439] • "Cases where bonds form rings"

[0440] In this specification, the phrase "one or more groups of two or more adjacent elements bonded together to form a substituted or unsubstituted monocyclic ring, or bonded together to form a substituted or unsubstituted fused ring, or not bonded together" refers to the cases of "one or more groups of two or more adjacent elements bonded together to form a substituted or unsubstituted monocyclic ring," "one or more groups of two or more adjacent elements bonded together to form a substituted or unsubstituted fused ring," and "one or more groups of two or more adjacent elements not bonded together."

[0441] The following description addresses the cases of "a substituted or unsubstituted monocyclic ring formed by the mutual bonding of one or more groups consisting of two or more adjacent elements" and "a substituted or unsubstituted fused ring formed by the mutual bonding of one or more groups consisting of two or more adjacent elements" (hereinafter, these cases are sometimes collectively referred to as "the case of forming a ring by bonding"). The case of anthracene compounds represented by the following general formula (TEMP-103) with an anthracene ring as the parent skeleton will be used as an example.

[0442] [Chemistry 19]

[0443]

[0444] For example, in R 921~R 930 In the context of "a ring formed by bonding one or more groups of two or more adjacent elements together," a group consisting of two adjacent elements that constitutes one group refers to R. 921 With R 922 group, R 922 With R 923 group, R 923 With R 924 group, R 924 With R 930 group, R 930 With R 925 group, R 925 With R 926 group, R 926 With R 927 group, R 927 With R 928 group, R 928 With R 929 The group and R 929 With R 921 The group.

[0445] The phrase "one or more groups" indicates that two or more of the aforementioned groups consisting of two or more adjacent elements can simultaneously form a loop. For example, in R... 921 With R 922 They bond together to form a ring Q A At the same time R 925 With R 926 They bond together to form a ring Q B In the case of anthracene compounds represented by the general formula (TEMP-103), the anthracene compounds are represented by the following general formula (TEMP-104).

[0446] [Chemistry 20]

[0447]

[0448] The case of a ring formed by "groups of two or more adjacent elements" refers not only to the case of group bonding consisting of "two" adjacent elements as in the example above, but also to the case of group bonding consisting of "three or more" adjacent elements. For example, representing R... 921 With R 922 They bond together to form a ring Q A And R 922 With R 923 They bond together to form a ring Q C Thus, three adjacent (R) 921 R 922 and R 923When the groups of components Q are bonded together to form a ring and condensed within the anthracene matrix, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q... A and ring Q C Shared R 922 .

[0449] [Chemistry 21]

[0450]

[0451] The formed "single ring" or "fused ring" can be either a saturated or unsaturated ring, depending solely on the structure of the formed ring. Even when a "single ring" or "fused ring" is formed from "one of a group consisting of two adjacent rings," the "single ring" or "fused ring" can still form a saturated or unsaturated ring. For example, the ring Q formed in the general formula (TEMP-104) A and ring Q B These are referred to as "single ring" or "fused ring," respectively. Furthermore, the ring Q formed in the general formula (TEMP-105) A and ring Q C It is a "fused ring". The ring Q of the general formula (TEMP-105) A With ring Q C Through ring Q A With ring Q C They condense to form a fused ring. If the ring Q of the general formula (TMEP-104) A If it is a benzene ring, then ring Q A It is a single ring. If the ring Q of the general formula (TMEP-104) is... A If it is a naphthalene ring, then ring Q A It is a fused ring.

[0452] "Unsaturated rings" refer to aromatic hydrocarbon rings or aromatic heterocycles. "Saturated rings" refer to aliphatic hydrocarbon rings or non-aromatic heterocycles.

[0453] As a specific example of an aromatic hydrocarbon ring, a structure in which the group exemplified in specific example group G1 is terminated by a hydrogen atom can be given.

[0454] As a specific example of an aromatic heterocycle, the structure in which the aromatic heterocycle group is terminated by a hydrogen atom can be cited as a specific example in specific example group G2.

[0455] As a specific example of an aliphatic hydrocarbon ring, a structure in which the group exemplified in specific example group G6 is terminated by a hydrogen atom can be cited.

[0456] "Ring formation" means that a ring is formed solely by multiple atoms of the parent skeleton, or by multiple atoms of the parent skeleton forming a ring with one or more arbitrary elements. For example, the general formula (TEMP-104) shows R... 921 With R 922 The ring Q formed by mutual bonding A Indicated by R 921 The carbon atoms of the bonded anthracene skeleton, and R 922 A ring formed by carbon atoms in a bonded anthracene framework and one or more arbitrary elements. As a specific example, in anthracene... 921 With R 922 Forming ring Q A In the case of R 921 The carbon atoms of the bonded anthracene skeleton, and R 922 When the carbon atoms of the bonded anthracene skeleton, or four carbon atoms, form a monocyclic unsaturated ring, it is due to R 921 With R 922 The resulting ring is a benzene ring.

[0457] Unless otherwise specified in this specification, "any element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur. In the case of any element (e.g., in the case of carbon or nitrogen), bonds that do not form a ring may be terminated by hydrogen atoms or substituted by "any substituents" described later. In the case of any element other than carbon, the resulting ring is a heterocycle.

[0458] Unless otherwise specified in this specification, the number of "one or more arbitrary elements" constituting a monocyclic or fused ring is preferably two or more but less than 15, more preferably three or more but less than 12, and even more preferably three or more but less than 5.

[0459] Unless otherwise specified in this specification, "monocyclic" is preferred over "fused ring".

[0460] Unless otherwise specified in this specification, "unsaturated ring" is preferred over "saturated ring".

[0461] Unless otherwise specified in this specification, "monocyclic" is preferably a benzene ring.

[0462] Unless otherwise specified in this specification, the "unsaturated ring" is preferably a benzene ring.

[0463] Unless otherwise specified in this specification, in the case of "one or more of the group consisting of two or more adjacent atoms" "forming a substituted or unsubstituted monocyclic ring by mutual bonding" or "forming a substituted or unsubstituted fused ring by mutual bonding", it is preferable that one or more of the group consisting of two or more adjacent atoms form a substituted or unsubstituted "unsaturated ring" by mutual bonding, wherein the substituted or unsubstituted "unsaturated ring" is composed of a plurality of atoms of a parent skeleton and one or more but no more than 15 elements selected from the group consisting of carbon, nitrogen, oxygen and sulfur.

[0464] In the case of substituents in the aforementioned “monocyclic” or “fused-ring” structures, the substituents are, for example, the “arbitrary substituents” described later. Specific examples of substituents in the case of substituents in the aforementioned “monocyclic” or “fused-ring” structures are the substituents described in the “Substituents Described in this Specification” section above.

[0465] When the aforementioned "saturated ring" or "unsaturated ring" has substituents, the substituents are, for example, the "arbitrary substituents" described later. Specific examples of substituents when the aforementioned "monocyclic ring" or "fused ring" has substituents are the substituents described in the section "Substituents Described in this Specification" above.

[0466] The above explains the cases of "a single ring formed by bonding one or more groups of two or more adjacent elements together, with substitution or no substitution" and "a fused ring formed by bonding one or more groups of two or more adjacent elements together, with substitution or no substitution" ("the case of forming a ring by bonding").

[0467] Substituents in cases of "substituted or unsubstituted"

[0468] In one embodiment of this specification, the substituent in the case of "substituted or unsubstituted" (sometimes referred to as "arbitrary substituent" in this specification) is, for example, from...

[0469] Composed of unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0470] Unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0471] Unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0472] Unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0473] -Si(R 901 (R) 902 (R) 903 ),

[0474] -O-(R 904 ),

[0475] -S-(R 905 ),

[0476] -N(R 906 (R) 907 ),

[0477] Halogen atom, cyano group, nitro group,

[0478] Unsubstituted aryl groups with 6 to 50 carbon atoms, and

[0479] Selected groups from the group consisting of unsubstituted heterocyclic groups having 5 to 50 cyclic atoms, etc.

[0480] Here, R 901 ~R 907 Each independently

[0481] hydrogen atom,

[0482] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0483] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0484] A substituted or unsubstituted aryl group having 6 to 50 carbon atoms in the cyclic ring, or a substituted or unsubstituted heterocyclic group having 5 to 50 carbon atoms in the cyclic ring.

[0485] When there are more than 2 R 901 In the case of 2 or more R 901 Whether they are the same or different,

[0486] When there are more than 2 R 902 In the case of 2 or more R 902 Whether they are the same or different,

[0487] When there are more than 2 R 903 In the case of 2 or more R 903 Whether they are the same or different,

[0488] When there are more than 2 R 904 In the case of 2 or more R 904 Whether they are the same or different,

[0489] When there are more than 2 R 905 In the case of 2 or more R 905 Whether they are the same or different,

[0490] When there are more than 2 R 906 In the case of 2 or more R 906 Whether they are the same or different,

[0491] When there are more than 2 R907 In the case of 2 or more R 907 They are the same or different from each other.

[0492] In one embodiment, the substituent in the case of "substituted or unsubstituted" is from...

[0493] Composed of alkyl groups with 1 to 50 carbon atoms,

[0494] aryl groups with 6 to 50 carbon atoms in the ring, and

[0495] The selected group is composed of heterocyclic groups with 5 to 50 cyclic atoms.

[0496] In one embodiment, the substituent in the case of "substituted or unsubstituted" is from...

[0497] Composed of alkyl groups having 1 to 18 carbon atoms,

[0498] aryl groups with 6 to 18 carbon atoms, and

[0499] The selected group is composed of heterocyclic groups with 5 to 18 cyclic atoms.

[0500] Specific examples of each group of any of the above-mentioned substituents are the specific examples of substituents described in the section "Substituents described in this specification" above.

[0501] Unless otherwise specified in this specification, adjacent substituents may form a "saturated ring" or an "unsaturated ring" with each other, preferably a substituted or unsubstituted saturated five-membered ring, a substituted or unsubstituted saturated six-membered ring, a substituted or unsubstituted unsaturated five-membered ring, or a substituted or unsubstituted unsaturated six-membered ring, more preferably a benzene ring.

[0502] Unless otherwise specified in this specification, any substituent may further have substituents. Any further substituents of any substituent are the same as those described above.

[0503] In this specification, the numerical range referred to as "AA~BB" means the range included by taking the value AA before "AA~BB" as the lower limit and the value BB after "AA~BB" as the upper limit.

[0504] In this specification, the mathematical expression “A≥B” means that the value of A is equal to the value of B, or the value of A is greater than the value of B.

[0505] In this specification, the mathematical expression “A≤B” means that the value of A is equal to the value of B, or the value of A is less than the value of B.

[0506] [First Implementation]

[0507] (Organic electroluminescent device)

[0508] The organic electroluminescent device of this embodiment has an anode, a cathode, and a light-emitting region disposed between the anode and the cathode. The light-emitting region includes a first sensitization layer and a first light-emitting layer. The first sensitization layer contains a first host material and a first sensitizing material, and the first light-emitting layer contains a second host material and a first luminescent compound. The first host material and the second host material are different from each other, and the first sensitizing material and the first luminescent compound are different from each other. The lowest excitation singlet state energy S1(G1) of the first sensitizing material is different from the band gap T at 77 [K] of the first sensitizing material. 77K The difference ΔST(G1) between G1 and G1 satisfies the following mathematical expression (number 1).

[0509] ΔST(G1)=S1(G1)-T 77K (G1)<0.5eV…(Number 1)

[0510] Traditional organic EL devices have adopted a structure with two or more stacked light-emitting layers (hereinafter sometimes referred to as stacked light-emitting layers) as light-emitting layers. Spatially, the light-emitting layers that generate excitons when electrically excited are separated from the layers that exhibit TTF-based upconversion, thereby achieving high device efficiency.

[0511] However, in order to achieve low voltage, it is usually difficult to selectively generate only excited triplet states by electrical excitation, and in particular, it is difficult to obtain blue emission.

[0512] For example, in organic EL devices with a stacked light-emitting layer, the threshold voltage of a blue phosphor using TTF is around 2.7 eV, which is close to the energy level of the emitted light.

[0513] On the other hand, regarding the efficient generation of the excited triplet state, there are known elements (upconversion elements) using a stacked emitting layer with a phosphorescent complex as the sensitizing material, and there are also known elements that utilize upconversion to mediate the triplet energy transfer from the phosphorescent complex to the TTF molecule (see Non-Patent Literature 1). However, as mentioned above, the external quantum efficiency (EQE) of the element using the stacked emitting layer with the phosphorescent complex is low (around 0.024%).

[0514] Therefore, the inventors discovered that by satisfying the above mathematical formula (number 1) (ΔST(G1)=S1(G1)-T) 77K By introducing a first sensitizer (G1)<0.5eV) into the organic EL element of the stacked luminescent layer instead of the phosphorescent complex that functions as a sensitizer, the luminescence initiation voltage can be reduced while maintaining high luminous efficiency.

[0515] In the first sensitized material that satisfies the mathematical formula (number 1), the band gap T at the lowest excitation singlet energy S1(G1) and 77 [K] is shown. 77K The difference ΔST(G1) is relatively small. This means that the energy required for excitation to the triplet state can be reduced, thus reducing energy loss. The first sensitizing material is preferably a delayed fluorescence material.

[0516] On the other hand, phosphorescent complexes (such as Pt complexes) used as sensitizing materials have relatively low light absorption intensity in order to be excited to the triplet state. Therefore, to realize their function as sensitizing materials, it is necessary to increase the concentration of phosphorescent complexes in the film, or to excite the phosphorescent complexes with high energy even at the cost of energy loss. Regarding concentration, there is a problem that phosphorescent complexes are prone to concentration quenching, thus making it impossible to increase the concentration of phosphorescent complexes in the film.

[0517] In contrast, the first sensitizing material (preferably a delayed fluorescence material) of this embodiment absorbs energy to become an excited triplet state, including the pathway mediating the excited singlet state. Furthermore, the light absorption intensity of the first sensitizing material is greater than that of the phosphorescent complex. Therefore, compared to the phosphorescent complex, the first sensitizing material of this embodiment can efficiently generate an excited state within the film even with a reduced concentration. Moreover, the first sensitizing material of this embodiment has a smaller ΔST, thus suppressing energy loss.

[0518] Thus, the first sensitizing material of this embodiment has a small ΔST in principle and a higher light absorption intensity than the phosphorescent complex, and therefore has the properties suitable for use as a sensitizing material.

[0519] Therefore, the organic EL element according to this embodiment emits light with a low light-emitting start voltage and high efficiency.

[0520] Specifically, for example, in the organic EL devices of Examples 1 to 12 described later, light emission with an external quantum efficiency (EQE) of 2.2% or higher and a density of 0.01 cd / m² can be obtained. 2 The luminescence initiation voltage of the organic EL elements is between 2.40V and 2.50V. The EQE of the organic EL elements in Examples 1-12 described later is approximately 1000 times that of the upconversion element in Non-Patent Document 1. The luminescence initiation voltage of the organic EL elements in Examples 1-12 described later is approximately equivalent to the band gap of the material used as the first sensitizing material.

[0521] As described above, the organic EL element of this embodiment is expected to meet the demand for low power consumption.

[0522] In one embodiment of this invention, the lowest excitation singlet energy S1(G1) of the first sensitizing material is related to the band gap T of the first sensitizing material at 77 [K]. 77K The difference ΔST(G1) satisfies any of the following mathematical expressions (Mathematics 11A) to (Mathematics 11D).

[0523] ΔST(G1)=S1(G1)-T 77K (G1)<0.4eV…(Figure 11A)

[0524] ΔST(G1)=S1(G1)-T 77K (G1)<0.3eV…(Figure 11B)

[0525] ΔST(G1)=S1(G1)-T 77K (G1)<0.2eV…(Figure 11C)

[0526] ΔST(G1)=S1(G1)-T 77K (G1)<0.1eV…(Figure 11D)

[0527] In one embodiment of this invention, the bandgap T of the first sensitized material at 77 [K] is... 77K (G1), the bandgap T of the first host material at 77K. 77K (H1), and the band gap T at 77 [K] of the second host material. 77K (H2) satisfies the following mathematical expression (number 2).

[0528] T 77K (G1)>T 77K (H1)>T 77K (H2)…(Number 2)

[0529] By making the first host material, the first sensitizing material, and the second host material satisfy the relationship of the mathematical formula (number 2), the triplet excitons generated in the first sensitizing layer move on the first host material instead of on the first sensitizing material with higher triplet energy, and thus easily move from the first host material to the second host material in the first luminescent layer.

[0530] In one embodiment of this invention, the bandgap T of the first sensitized material at 77 [K] is... 77K (G1) and the band gap T at 77 [K] of the first host material 77K (H1) satisfies the following mathematical expression (number 21).

[0531] T 77K (G1)-T 77K (H1)<0.5eV…(Number 21)

[0532] In one embodiment of this invention, the bandgap T of the first sensitized material at 77 [K] is... 77K (G1) and the band gap T at 77 [K] of the first host material 77K (H1) satisfies the following mathematical expression (number 21A).

[0533] T 77K (G1)-T 77K (H1)<0.4eV…(Figure 21A)

[0534] By making the first sensitizing material and the first host material satisfy the relationship of the mathematical formula (number 21) or (number 21A), the triplet excitons generated in the first sensitizing layer can easily move from the first sensitizing material to the first host material efficiently.

[0535] In one embodiment of this invention, the band gap T of the first host material at 77 K is... 77K (H1) and the band gap T of the second host material at 77 [K] 77K (H2) satisfies the following mathematical expression (number 22).

[0536] T 77K (H1)-T 77K (H2)<0.3eV…(Number 22)

[0537] By making the first host material and the second host material satisfy the relationship of the mathematical formula (number 22), the triplet energy is excited to move efficiently from the first sensitized layer containing the first host material to the first luminescent layer containing the second host material, which advantageously reflects the upconversion in the luminescent region.

[0538] In one embodiment of this invention, the lowest excitation singlet energy S1(G1) of the first sensitizing material and the lowest excitation singlet energy S1(BD1) of the first luminescent compound satisfy the following mathematical expression (Equation 3).

[0539] S1(BD1)>S1(G1)…(Number 3)

[0540] By making the first sensitizing material and the first luminescent compound satisfy the relationship of the mathematical formula (number 3), the first sensitizing layer is given an energy lower than the lowest excitation singlet energy of the first luminescent compound, thereby demonstrating the upconversion luminescence of the organic EL element.

[0541] In one embodiment of this invention, the first sensitized layer is directly connected to the first light-emitting layer.

[0542] In one embodiment, the first sensitization layer is disposed between the anode and the cathode, and the first light-emitting layer is disposed between the first sensitization layer and the cathode. In this embodiment, the light-emitting region sequentially includes the first sensitization layer and the first light-emitting layer from the anode side.

[0543] In one embodiment of this invention, when the light-emitting region includes a first sensitization layer and a first light-emitting layer sequentially from the anode side,

[0544] The absolute value of the lowest unoccupied orbital energy level LUMO(G1) of the first sensitized material and the absolute value of the lowest unoccupied orbital energy level LUMO(H1) of the first host material satisfy the following mathematical expression (Equation 4).

[0545] |LUMO(G1)|>|LUMO(H1)|…(Number 4)

[0546] By making the first sensitizing material and the first host material satisfy the relationship of the mathematical formula (number 4), electrons in the first sensitizing layer are easily captured by the first sensitizing material, resulting in the promotion of recombination of holes and electrons in the first sensitizing layer.

[0547] In one embodiment of this invention, when the light-emitting region includes a first sensitization layer and a first light-emitting layer sequentially from the anode side, in addition to the first sensitization material and the first host material satisfying the relationship of the mathematical formula (number 4), the absolute value of the lowest unoccupied orbital energy level LUMO (H2) of the second host material and the absolute value of the lowest unoccupied orbital energy level LUMO (BD1) of the first luminescent compound satisfy the relationship of the following mathematical formula (number 41).

[0548] |LUMO(H2)|>|LUMO(BD1)|…(Number 41)

[0549] By making the second host material and the first luminescent compound satisfy the relationship of the mathematical formula (number 41), electrons in the first luminescent layer are difficult to be captured by the first luminescent compound. As a result, the recombination of holes and electrons in the first sensitized layer is promoted.

[0550] In one embodiment, the first sensitization layer is disposed between the anode and the cathode, and the first light-emitting layer is disposed between the first sensitization layer and the anode. In this embodiment, the light-emitting region sequentially includes the first light-emitting layer and the first sensitization layer from the anode side.

[0551] In one embodiment of this invention, where the light-emitting region sequentially includes a first light-emitting layer and a first sensitizing layer from the anode side,

[0552] The absolute value of the highest occupied orbital energy level HOMO(G1) of the first sensitized material and the absolute value of the highest occupied orbital energy level HOMO(H1) of the first host material satisfy the following mathematical expression (Equation 5).

[0553] |HOMO(G1)|<|HOMO(H1)|…(Number 5)

[0554] By making the first sensitizing material and the first host material satisfy the relationship of the mathematical formula (number 5), holes in the first sensitizing layer are easily captured by the first sensitizing material, resulting in the promotion of recombination between holes and electrons in the first sensitizing layer.

[0555] In one embodiment, when the light-emitting region includes a first light-emitting layer and a first sensitizing layer sequentially from the anode side, in addition to the first sensitizing material and the first host material satisfying the relationship of the mathematical formula (number 5),

[0556] The absolute value of the highest occupied orbital energy level HOMO(H2) of the second host material and the absolute value of the highest occupied orbital energy level HOMO(BD1) of the first luminescent compound satisfy the following mathematical expression (number 51).

[0557] |HOMO(H2)|<|HOMO(BD1)|…(Number 51)

[0558] By making the second host material and the first luminescent compound satisfy the relationship of the mathematical formula (number 51), holes in the first luminescent layer are difficult to be captured by the first luminescent compound, resulting in the promotion of recombination of holes and electrons in the first sensitized layer.

[0559] The measurement methods for HOMO and LUMO are described below.

[0560] (Highest occupied orbital energy level HOMO)

[0561] For the highest occupied orbital level HOMO, the target compound (compound or material) is irradiated with light, and the amount of electrons generated by charge separation at this time is measured using an atmospheric photoelectron spectrometer (manufactured by Riken Keiki Co., Ltd.: AC-3).

[0562] (Lowest unoccupied orbital level LUMO)

[0563] The lowest unoccupied orbital (LUMO) level was measured using differential pulse voltammetry. Details of differential pulse voltammetry are as follows.

[0564] The lowest unoccupied orbital (LUMO) of an object (compound or material) is calculated using the following mathematical formula (Equation 1Y). The unit of the LUMO is eV.

[0565] LUMO=-1.19×(Ere-Efc)-4.78eV…(number 1Y)

[0566] In the mathematical expression (number 1Y), Ere and Efc are as follows.

[0567] Ere: First reduction potential (DPV, reverse scan) of the measured object

[0568] Efc: First oxidation potential of ferrocene (DPV, positive scan), (ca. +0.55V vs Ag / AgCl)

[0569] The redox potentials were measured using an electrochemical analyzer (ALS: CHI852D) via differential pulse voltammetry (DPV).

[0570] The sample solution used in the measurement was prepared as follows: The analyte was dissolved at a concentration of 1.0 mmol / L using N,N-dimethylformamide (DMF) as the solvent, and tetrabutylammonium hexafluorophosphate (TBHP) as the supporting electrolyte was dissolved at a concentration of 100 mmol / L. A glassy carbon electrode was used as the working electrode. A platinum (Pt) electrode was used as the counter electrode.

[0571] (References) METhompson et al., Organic Electronics, 6 (2005), pp. 11-20; Organic Electronics, 10 (2009), pp. 515-520.

[0572] In one embodiment of this invention, the energy E of the peak of the emission spectrum in the organic electroluminescent element is... PE (eV) and obtained 0.01cd / m 2 The brightness is the energy E given to the element TH The difference (eV) satisfies the following mathematical expression (number 6).

[0573] E TH -E PE ≤0.05eV…(number 6)

[0574] In this specification, the light-emitting initiation voltage V TH (Unit: V) refers to a yield of 0.01 cd / m³. 2The voltage when the current density drives the element to achieve the desired brightness.

[0575] In this specification, "0.01 cd / m" is obtained. 2 The brightness is the energy E given to the element TH "(eV)" refers to the value calculated using the following mathematical formula (number Y1).

[0576] E TH (eV) = Light-emitting initiation voltage (V) TH (V) × elementary charge (e) … (number Y1)

[0577] In this specification, "the energy E of the peak of the emission spectrum" PE "(eV)" refers to the energy (unit: eV) required to excite the luminescent compound contained in the luminescent layer of the measured object to the excited singlet state S1. "E" represents the energy of the peak in the emission spectrum. PE "(eV)" is essentially equivalent to the band gap of a luminescent compound.

[0578] Light-emitting initiation voltage V TH The measurement method is as described in the examples.

[0579] In this specification, "the energy E of the peak of the emission spectrum" PE "(eV)" refers to the measured value of the lowest excitation singlet energy S1 of the luminescent compound contained in the luminescent layer of the object being measured. The method for measuring the lowest excitation singlet energy S1 is as described in the examples.

[0580] An example of the light emission mechanism of this embodiment will be described.

[0581] Figure 1 This diagram illustrates the light-emitting mechanism of the stacked light-emitting layer in this embodiment. Figure 2A This diagram illustrates the luminescence mechanism of a fluorescent luminescent layer (monolayer). Figure 2B This is a diagram used to illustrate the light emission mechanism of a stacked light-emitting layer containing a Pt complex.

[0582] Figure 1 , Figure 2A and Figure 2B In this embodiment, TADF represents a delayed fluorescence material (equivalent to a first sensitizing material), BH1 represents a first host material, BH2 represents a second host material, BH represents the host material in the fluorescent luminescent layer (monolayer), BD represents a luminescent compound (equivalent to a first luminescent compound in this embodiment), and V TH This indicates the voltage at which light emission begins.

[0583] (An example of the light-emitting mechanism in this embodiment)

[0584] Figure 1 The TADF (delayed fluorescence material) shown is, for example, the compound TADF-a used in Example 1 described later, with a band gap of approximately 2.4 eV. Therefore, by... Figure 1 The stacked luminescent layer imparts an energy of approximately 2.4 eV, exciting the TADF (delayed fluorescence material) in the first sensitization layer. This approximately 2.4 eV corresponds to the energy E of the peak of the emission spectrum in the mathematical formula (C16). PE (eV).

[0585] As described above, by imparting an energy equivalent to the band gap of a TADF (delayed fluorescence material), an excited singlet state S1 and an excited triplet state T1 of the TADF are generated. However, since the TADF also satisfies the aforementioned mathematical formula (number 1), the excited singlet state S1 of the TADF intersystem jumps to the excited triplet state T1 with less energy loss. The excited triplet state T1 generated through intersystem jumping transfers energy to the first host material (BH1) in the first sensitization layer, and then to the second host material (BH2) in the first luminescent layer (the aforementioned mathematical formula (number 2)). In the second host material (BH2), a TTF phenomenon occurs, and the excited triplet state T1 of the second host material (BH2) is converted into the excited singlet state S1. The energy of the converted excited singlet state S1 is transferred to the luminescent compound (BD), whose excited singlet state S1 is higher than that of TADF (delayed fluorescence material) (as stated in equation (3)). Therefore, the luminescent compound (BD) emits blue light with an energy of approximately 2.4 eV (luminescence initiation voltage V). TH ≈2.4V). This approximately 2.4eV corresponds to 0.01cd / m² in the mathematical expression (number 6). 2 The brightness is the energy E given to the element TH (eV).

[0586] Thus, in the luminescence mechanism of this embodiment, by simply imparting energy to the stacked luminescent layer sufficient to excite the TADF (delayed fluorescence material), almost all the excited triplet states generated during the intersystem crossing of the TADF can be moved to the first luminescent layer, enabling the luminescent compound (BD) to emit blue light. That is, Figure 1 The stacked light-emitting layer shown can achieve an energy equivalent to the band gap of TADF (delayed fluorescence material) (E in the mathematical formula (number 6)). PE This causes the stacked light-emitting layer to emit blue light, so it can be said to be a light-emitting layer that can embody upconversion.

[0587] Therefore, the emission onset voltage V of an organic EL device having this stacked light-emitting layer is... TH It emits light with low efficiency.

[0588] (The luminescence mechanism of a single-layer fluorescent luminescent layer)

[0589] Figure 2A The luminescent compound (BD) shown is a blue luminescent compound. Figure 2A In this case, by imparting energy to the monolayer fluorescent luminescent layer to excite the blue luminescent compound (the band gap of the blue luminescent compound is about 2.7 eV), the luminescent compound (BD) becomes an excited singlet state S1 through direct recombination of charges on BD, and the blue luminescent compound emits blue light.

[0590] (Light emission mechanism of stacked light-emitting layers)

[0591] exist Figure 2B In this case, by imparting an energy (the band gap of the Pt complex is about 2.4 eV) to the stacked light-emitting layer to excite the Pt complex, which is a phosphorescent complex, the Pt complex is excited.

[0592] Subsequent light-emitting mechanisms and Figure 1 The luminescence mechanism is the same, but the light absorption intensity of the Pt complex is low and it is prone to concentration quenching. Therefore, the energy used to excite the Pt complex alone cannot make the luminescent compound (BD) emit blue light.

[0593] In order for the luminescent compound (BD) to emit blue light, it is necessary to improve the... Figure 2B The energy imparted by the stacked light-emitting layer, as shown, or the concentration of the Pt complex, is increased. Therefore, organic EL devices with stacked light-emitting layers containing Pt complexes cannot emit light efficiently.

[0594] exist Figure 3 A schematic configuration of an example of an organic EL element according to the first embodiment is shown.

[0595] The organic EL element 1 includes a light-transmitting substrate 2, an anode 3, a cathode 4, and an organic layer disposed between the anode 3 and the cathode 4. The organic layer is composed of a hole injection layer 6, a hole transport layer 7, a first sensitization layer 51, a first light-emitting layer 52, an electron transport layer 8, and an electron injection layer 9, sequentially stacked from the anode 3 side. The light-emitting region 5 includes the first sensitization layer 51 and the first light-emitting layer 52 sequentially from the anode 3 side. The first sensitization layer 51 and the first light-emitting layer 52 are preferably directly connected.

[0596] Figure 4 A schematic configuration of another example of the organic EL element of the first embodiment is shown.

[0597] The organic EL element 1A includes a light-transmitting substrate 2, an anode 3, a cathode 4, and an organic layer disposed between the anode 3 and the cathode 4. The organic layer is composed of a hole injection layer 6, a hole transport layer 7, a first light-emitting layer 52, a first sensitizing layer 51, an electron transport layer 8, and an electron injection layer 9, sequentially stacked from the anode 3 side. The light-emitting region 5A includes the first light-emitting layer 52 and the first sensitizing layer 51 sequentially from the anode 3 side. The first light-emitting layer 52 and the first sensitizing layer 51 are preferably directly connected.

[0598] This invention is not limited to Figure 3 and Figure 4 The diagram shows the configuration of an organic EL element. Other configurations of organic EL elements include, for example, an organic EL element with an interlayer disposed between the first sensitized layer 51 and the first light-emitting layer 52. Figure 3 In this case, the light-emitting region 5 can sequentially include a first sensitization layer 51, an intercalation layer, and a first light-emitting layer 52, starting from the anode 3 side. Figure 4 In this case, the light-emitting region 5A can be sequentially comprised from the anode 3 side, including the first light-emitting layer 52, the intercalation layer, and the first sensitization layer 51.

[0599] The configuration of the organic EL element according to the first embodiment will be described. Hereinafter, the description of the reference numerals in the drawings will sometimes be omitted.

[0600] (Emitting area)

[0601] The organic EL element of this embodiment has a light-emitting region including a first sensitization layer and a first light-emitting layer. The light-emitting region of this embodiment may include only the first sensitization layer and the first light-emitting layer, or it may include an organic layer different from the first sensitization layer and the first light-emitting layer.

[0602] (First sensitization layer)

[0603] The first sensitization layer contains a first host material and a first sensitization material.

[0604] The first host material and the second host material are different compounds. The first sensitizing material and the first luminescent compound are different compounds.

[0605] As a first main material, for example, at least one compound selected from the group consisting of the first compound and the second compound described below can be cited.

[0606] As the first sensitizing material, there is no particular limitation as long as the compound satisfies the mathematical formula (number 1). For example, at least one compound selected from the group consisting of compounds represented by the following general formulas (2), (22) and (11) to (13), (1000) to (1003), (1004A) to (1004D), (1005A) to (1005D), (1006), (1007A), (1007B), (1008), (1008A), (1009A) to (1009C), (1010), (1011A), (1011B), (1012A), (1012B), (1013) to (1015), (1016A) and (1016B) can be cited.

[0607] In one embodiment of this invention, the first sensitizing material is not a complex.

[0608] In one embodiment of this invention, the first sensitizing material does not contain heavy metal elements. Examples of heavy metal elements include iridium, osmium, and platinum.

[0609] In one embodiment of this invention, the first sensitized layer does not contain metal complexes.

[0610] In one embodiment of this invention, the first sensitization layer does not contain heavy metal elements.

[0611] In one embodiment, the first sensitizing material is a compound exhibiting delayed fluorescence (delayed fluorescence material). In another embodiment, the first sensitizing material is a compound that does not exhibit delayed fluorescence.

[0612] In one embodiment of this invention, the first sensitized layer contains a first sensitizing material at a mass percentage of 10% or more or a mass percentage of 25% or more of the total mass of the first sensitized layer.

[0613] In one embodiment of this invention, the first sensitized layer contains a first sensitizing material at a rate of 50% or less or 25% or less of the total mass of the first sensitized layer.

[0614] In one embodiment of this invention, the first sensitized layer contains the first host material at a mass percentage of 50% or more, 60% or more, 70% or more, 80% or more, 90% or more, or 95% or more of the total mass of the first sensitized layer.

[0615] In one embodiment of this invention, the first sensitized layer contains a first host material at a mass percentage of less than 90% of the total mass of the first sensitized layer.

[0616] In one embodiment of this invention, the upper limit of the total content of the first host material and the first sensitizing material in the first sensitizing layer is 100% by mass.

[0617] In one embodiment of this invention, the thickness of the first sensitized layer is 3 nm or more, or 5 nm or more. If the thickness of the first sensitized layer is 3 nm or more, it is sufficient to induce recombination of holes and electrons in the first sensitized layer.

[0618] In one embodiment, the thickness of the first sensitization layer is 20 nm or less or 15 nm or less. If the thickness of the first sensitization layer is 20 nm or less, it is a sufficiently thin thickness to allow the triplet exciton to move toward the first emitting layer.

[0619] (First sensitizing material)

[0620] In one embodiment of this invention, the first sensitizing material is a compound represented by the following general formula (2) or the following general formula (22).

[0621] Compounds represented by general formula (2)

[0622] [Chemistry 22]

[0623]

[0624] (in the general formula (2),

[0625] n is 1, 2, 3, or 4.

[0626] m is 1, 2, 3, or 4.

[0627] q is 0, 1, 2, 3, or 4.

[0628] m+n+q=6,

[0629] CN stands for cyano group.

[0630] D1 is a group represented by the following general formula (2a), general formula (2b), or general formula (2c). When there are multiple D1 groups, the multiple D1 groups may be the same or different from each other.

[0631] One or more groups consisting of two or more adjacent elements in Rx

[0632] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[0633] They bond to each other to form substituted or unsubstituted fused rings.

[0634] When there are multiple Rx instances, these Rx instances may be the same or different from each other.

[0635] The Rx values ​​for both the substituted and unsubstituted monocyclic rings and the fused rings that do not form the substituted or unsubstituted rings are independently [values ​​to be filled in].

[0636] hydrogen atom,

[0637] Halogen atoms,

[0638] substituted or unsubstituted aryl groups with 6 to 30 carbon atoms

[0639] Heterocyclic groups with 5 to 30 cyclic atoms, substituted or unsubstituted

[0640] Substituted or unsubstituted amino groups

[0641] Substituted or unsubstituted carbonyl groups

[0642] Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms

[0643] Substituted or unsubstituted alkyl halides with 1 to 30 carbon atoms

[0644] Substituted or unsubstituted cycloalkyl groups with 3 to 30 carbon atoms

[0645] Substituted or unsubstituted alkylsilyl groups having 3 to 30 carbon atoms, or

[0646] Substituted or unsubstituted arylsilyl groups with 6 to 60 carbon atoms in the cyclic structure.

[0647] CN, D1, and Rx are bonded to carbon atoms in a six-membered ring, respectively.

[0648] [Chemistry 23]

[0649]

[0650] (in the general formula (2a),

[0651] One or more groups consisting of two or more adjacent elements from R1 to R8

[0652] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[0653] They bond to each other to form substituted or unsubstituted fused rings.

[0654] R1 to R8, which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted fused ring, are each independently...

[0655] hydrogen atom,

[0656] Halogen atoms,

[0657] substituted or unsubstituted aryl groups with 6 to 30 carbon atoms

[0658] Heterocyclic groups with 5 to 30 cyclic atoms, substituted or unsubstituted

[0659] Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms

[0660] Substituted or unsubstituted alkyl halides with 1 to 30 carbon atoms

[0661] Substituted or unsubstituted cycloalkyl groups with 3 to 30 carbon atoms

[0662] Substituted or unsubstituted alkylsilyl groups with 3 to 30 carbon atoms

[0663] Substituted or unsubstituted arylsilyl groups with 6 to 60 carbon atoms,

[0664] hydroxyl,

[0665] Alkoxy groups with 1 to 30 carbon atoms, whether substituted or unsubstituted.

[0666] Substituted or unsubstituted haloalkoxy groups with 1 to 30 carbon atoms

[0667] Substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms in the cyclic group,

[0668] Substituted or unsubstituted alkylamino groups with 2 to 30 carbon atoms

[0669] substituted or unsubstituted arylamino groups with 6 to 60 carbon atoms in the cyclic formation,

[0670] Thiol group,

[0671] Substituted or unsubstituted alkylthio groups having 1 to 30 carbon atoms, or

[0672] Arylthio groups with 6 to 30 carbon atoms, either substituted or unsubstituted.

[0673] * indicates the site where the carbon atom of the six-membered ring in the general formula (2) is bonded.

[0674] [Chemistry 24]

[0675]

[0676] (in the general formula (2b),

[0677] By R 21 ~R 28 One or more groups consisting of two or more adjacent elements.

[0678] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[0679] They bond to each other to form substituted or unsubstituted fused rings.

[0680] R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 21 ~R 28 Each of these is independently synonymous with R1 to R8 in the general formula (2a).

[0681] A represents a ring structure represented by the following general formula (211) or the following general formula (212), which is condensed with an adjacent ring structure at any position.

[0682] p is 1, 2, 3, or 4.

[0683] When p is 2, 3, or 4, multiple ring structures A may be identical or different from each other.

[0684] * indicates the site where the carbon atom of the six-membered ring in the general formula (2) is bonded.

[0685] [Chemistry 25]

[0686]

[0687] (in the general formula (2c),

[0688] By R 2001 ~R 2008 One or more groups consisting of two or more adjacent elements.

[0689] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[0690] They bond to each other to form substituted or unsubstituted fused rings.

[0691] R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 2001 ~R 2008 Each of them is independently synonymous with R1 to R8, which are substituents in the general formula (2a).

[0692] B represents a ring structure represented by the following general formula (211) or the following general formula (212), which is condensed with the adjacent ring structure at any position.

[0693] px can be 1, 2, 3, or 4.

[0694] When px is 2, 3, or 4, multiple ring structures B may be the same or different from each other.

[0695] C represents a ring structure represented by the following general formula (211) or the following general formula (212), which is condensed with an adjacent ring structure at any position.

[0696] py is 1, 2, 3 or 4,

[0697] When py is 2, 3, or 4, multiple ring structures C may be the same or different from each other.

[0698] * indicates the site where the carbon atom of the six-membered ring in the general formula (2) is bonded.

[0699] [Chemistry 26]

[0700]

[0701] (in the general formula (211),

[0702] By R 2009 and R 2010 The group

[0703] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[0704] They bond to each other to form substituted or unsubstituted fused rings, or

[0705] It bonds with a portion of an adjacent ring structure to form a ring.

[0706] In the general formula (212), X 201 For CR 2011 R 2012 NR 2013 sulfur atoms or oxygen atoms

[0707] By R 2011 and R 2012 The group

[0708] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[0709] They bond to each other to form substituted or unsubstituted fused rings.

[0710] R 2013 R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 2009 R 2010 R 2011 and R 2012 Each of the substituents R1 to R8 in the general formula (2a) is independently synonymous with one of them.

[0711] In general formula (211), R 2009 and R 2010 To form a ring by independently bonding with a portion of an adjacent ring structure, specifically referring to any of the following cases (I) to (IV).

[0712] Furthermore, in general formula (211), R 2009 and R 2010 The groups that make up the ring are bonded together to form a ring, specifically referring to the following (V).

[0713] (I) When the ring structures represented by general formula (211) are adjacent to each other, the R of one of the two adjacent rings2009 and another ring of R 2009 A group, a ring of R 2009 and another ring of R 2010 The group, and a ring of R 2010 and another ring of R 2010 A ring is formed by bonding any one or more groups within a group together.

[0714] (II) The ring structure represented by general formula (211) and the one with R in general formula (2b) 25 ~R 28 In the case of adjacent benzene rings, the R of one of the two adjacent rings 2009 and another ring of R 25 A group, a ring of R 2009 and another ring of R 28 A group, a ring of R 2010 and another ring of R 25 The group, and a ring of R 2010 and another ring of R 28 A ring is formed by bonding any one or more groups within a group together.

[0715] (III) The ring structure represented by general formula (211) and the one with R in general formula (2c) 2001 ~R 2004 In the case of adjacent benzene rings, the R of one of the two adjacent rings 2009 and another ring of R 2001 A group, a ring of R 2009 and another ring of R 2004 A group, a ring of R 2010 and another ring of R 2001 The group, and a ring of R 2010 and another ring of R 2004 A ring is formed by bonding any one or more groups within a group together.

[0716] (IV) The ring structure represented by general formula (211) and the one with R in general formula (2c) 2005 ~R 2008 In the case of adjacent benzene rings, the R of one of the two adjacent rings 2009 and another ring of R 2005 A group, a ring of R 2009 and another ring of R 2008 A group, a ring of R 2010 and another ring of R 2005 The group, and a ring of R 2010 and another ring of R 2008 A ring is formed by bonding any one or more groups within a group together.

[0717] (V) R, represented by the ring structure in general formula (211) 2009 and R 2010 The groups that make up the ring are bonded together to form a loop. That is, (V) refers to R formed by bonds to the same loop. 2009 and R 2010 The components bond together to form a ring.

[0718] In the general formula (2), Rx is preferably a hydrogen atom, an unsubstituted aryl group with 6 to 30 cyclic carbon atoms, an unsubstituted heterocyclic group with 5 to 30 cyclic carbon atoms, or an unsubstituted alkyl group with 1 to 30 cyclic carbon atoms.

[0719] When Rx is an unsubstituted heterocyclic group with 5 to 30 cyclic atoms, it is preferable that Rx, which is an unsubstituted heterocyclic group with 5 to 30 cyclic atoms, is pyridinyl, pyrimidinyl, triazine, dibenzofuranyl, or dibenzothiophene.

[0720] In this specification, triazine group refers to a group obtained by removing one hydrogen atom from 1,3,5-triazine, 1,2,4-triazine or 1,2,3-triazine.

[0721] The triazine group is preferably a group obtained by removing one hydrogen atom from 1,3,5-triazine.

[0722] In the general formula (2), more preferably Rx is independently a hydrogen atom, an unsubstituted aryl group with 6 to 30 cyclic carbon atoms, an unsubstituted dibenzofuranyl group, or an unsubstituted dibenzothiophene group.

[0723] In the general formula (2), Rx is preferably a hydrogen atom.

[0724] In the general formula (2), R1 to R8 and R are preferred as substituents. 21 ~R 28 R 2001 ~R 2008 R 2009 ~R 2010 and R 2011 ~R 2013 Each of the following can be independently an unsubstituted aryl group having 6 to 30 carbon atoms, an unsubstituted heterocyclic group having 5 to 30 carbon atoms, or an unsubstituted alkyl group having 1 to 30 carbon atoms.

[0725] In the general formula (2), D1 is preferably any one of the groups represented by the following general formulas (D-21) to (D-37).

[0726] • Groups represented by general formulas (D-21) to (D-25)

[0727] [Chemistry 27]

[0728]

[0729] [Chemistry 28]

[0730]

[0731] (In the general formulas (D-21) to (D-25),

[0732] By R 171 ~R 180 One or more groups consisting of two or more adjacent elements.

[0733] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[0734] They bond to each other to form substituted or unsubstituted fused rings.

[0735] By R 181 ~R 190 One or more groups consisting of two or more adjacent elements.

[0736] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[0737] They bond to each other to form substituted or unsubstituted fused rings.

[0738] By R 191 ~R 200 One or more groups consisting of two or more adjacent elements.

[0739] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[0740] They bond to each other to form substituted or unsubstituted fused rings.

[0741] By R 71 ~R 82 One or more groups consisting of two or more adjacent elements.

[0742] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[0743] They bond to each other to form substituted or unsubstituted fused rings.

[0744] By R 83 ~R 90 One or more adjacent groups in a loop are bonded together to form a substituted or unsubstituted monocycle, or

[0745] They bond to each other to form substituted or unsubstituted fused rings.

[0746] R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 171 ~R 200 and R 71 ~R 90 Each independently

[0747] hydrogen atom,

[0748] Halogen atoms,

[0749] substituted or unsubstituted aryl groups with 6 to 14 carbon atoms

[0750] Substituted or unsubstituted heterocyclic groups with 5 to 14 cyclic atoms

[0751] Substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms

[0752] Substituted or unsubstituted alkyl halides with 1 to 30 carbon atoms

[0753] Substituted or unsubstituted cycloalkyl groups with 3 to 30 carbon atoms

[0754] Substituted or unsubstituted alkylsilyl groups having 3 to 6 carbon atoms

[0755] hydroxyl,

[0756] Substituted or unsubstituted alkoxy groups having 1 to 6 carbon atoms

[0757] Substituted or unsubstituted haloalkoxy groups having 1 to 6 carbon atoms

[0758] Substituted or unsubstituted aryloxy groups with 6 to 14 carbon atoms,

[0759] Substituted or unsubstituted alkylamino groups with 2 to 12 carbon atoms

[0760] Thiol group,

[0761] Substituted or unsubstituted alkylthio groups having 1 to 30 carbon atoms, or

[0762] Arylthio groups, substituted or unsubstituted, with 6 to 14 carbon atoms in the cyclic group.

[0763] * indicates the site where the carbon atom of the six-membered ring in the general formula (2) is bonded.

[0764] In the general formula (2), R is preferably used as a substituent. 171 ~R 200 and R 71 ~R 90 Each is independently an unsubstituted aryl group having 6 to 14 cyclic carbon atoms, an unsubstituted heterocyclic group having 5 to 14 cyclic carbon atoms, or an unsubstituted alkyl group having 1 to 6 cyclic carbon atoms.

[0765] In the general formula (2), R is also preferred. 171 ~R 200 and R 71 ~R 90 It is a hydrogen atom.

[0766] Preferably, the group represented by the general formula (D-21) to (D-25) is any one of the groups represented by the general formulas (2-5) to (2-14) below.

[0767] [Chemistry 29]

[0768]

[0769] [Chemistry 30]

[0770]

[0771] In the general formulas (2-5) to (2-14), * indicates the site where the carbon atom of the six-membered ring in the general formula (2) is bonded.

[0772] • Groups represented by general formulas (D-26) to (D-31)

[0773] [Chemistry 31]

[0774]

[0775] [Chemistry 32]

[0776]

[0777] [Chemistry 33]

[0778]

[0779] (In the general formulas (D-26) to (D-31),

[0780] By R 101 ~R 110 One or more groups consisting of two or more adjacent elements.

[0781] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[0782] They bond to each other to form substituted or unsubstituted fused rings.

[0783] By R 111 ~R 120 One or more groups consisting of two or more adjacent elements.

[0784] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[0785] They bond to each other to form substituted or unsubstituted fused rings.

[0786] By R 121 ~R 130 One or more groups consisting of two or more adjacent elements.

[0787] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[0788] They bond to each other to form substituted or unsubstituted fused rings.

[0789] By R 131 ~R 140 One or more groups consisting of two or more adjacent elements.

[0790] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[0791] They bond to each other to form substituted or unsubstituted fused rings.

[0792] By R 141 ~R 150 One or more groups consisting of two or more adjacent elements.

[0793] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[0794] They bond to each other to form substituted or unsubstituted fused rings.

[0795] By R 61 ~R 70 One or more groups consisting of two or more adjacent elements.

[0796] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[0797] They bond to each other to form substituted or unsubstituted fused rings.

[0798] R 11 ~R 16 R, and R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 101 ~R 150 and R 61 ~R 70 Each independently

[0799] hydrogen atom,

[0800] substituted or unsubstituted aryl groups with 6 to 14 carbon atoms

[0801] Substituted or unsubstituted heterocyclic groups with 5 to 14 cyclic atoms

[0802] Substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms

[0803] Substituted or unsubstituted alkyl halides with 1 to 30 carbon atoms

[0804] Substituted or unsubstituted cycloalkyl groups with 3 to 30 carbon atoms

[0805] Substituted or unsubstituted alkylsilyl groups having 3 to 6 carbon atoms

[0806] hydroxyl,

[0807] Substituted or unsubstituted alkoxy groups having 1 to 6 carbon atoms

[0808] Substituted or unsubstituted aryloxy groups with 6 to 14 carbon atoms,

[0809] substituted or unsubstituted arylamino groups with 6 to 28 carbon atoms in the cyclic formation,

[0810] Substituted or unsubstituted alkylamino groups with 2 to 12 carbon atoms

[0811] Thiol group,

[0812] Substituted or unsubstituted alkylthio groups having 1 to 6 carbon atoms, or

[0813] Substituted or unsubstituted arylthio groups with 6 to 14 carbon atoms in the cyclic formation.

[0814] R as a substituent 11 ~R 16 Each independently

[0815] Substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms

[0816] substituted or unsubstituted aryl groups with 6 to 14 carbon atoms

[0817] Substituted or unsubstituted heterocyclic groups with 5 to 14 cyclic atoms

[0818] Substituted or unsubstituted alkylsilyl groups having 3 to 6 carbon atoms

[0819] Substituted or unsubstituted aryloxy groups with 6 to 14 carbon atoms,

[0820] Substituted or unsubstituted alkylamino groups with 2 to 12 carbon atoms

[0821] Substituted or unsubstituted alkylthio groups having 1 to 6 carbon atoms, or

[0822] Arylthio groups, substituted or unsubstituted, with 6 to 14 carbon atoms in the cyclic group.

[0823] * indicates the site where the carbon atom of the six-membered ring in the general formula (2) is bonded.

[0824] In the general formula (2), R is preferably used as a substituent. 101 ~R 150 and R 61 ~R 70 They are, independently, an unsubstituted aryl group having 6 to 14 carbon atoms, an unsubstituted heterocyclic group having 5 to 14 carbon atoms, or an unsubstituted alkyl group having 1 to 6 carbon atoms.

[0825] R as a substituent 11 ~R 16 They are, independently, an unsubstituted aryl group with 6 to 14 cyclic carbon atoms, or an unsubstituted heterocyclic group with 5 to 14 cyclic atoms.

[0826] In the general formula (2), R is also preferred. 101 ~R 150 and R 61 ~R 70 R is a hydrogen atom, and it is a substituent. 11 ~R 16 They are, independently, an unsubstituted aryl group with 6 to 14 cyclic carbon atoms, or an unsubstituted heterocyclic group with 5 to 14 cyclic atoms.

[0827] • Groups represented by general formulas (D-32) to (D-37)

[0828] [Chemistry 34]

[0829]

[0830] [Chemistry 35]

[0831]

[0832] [Chemistry 36]

[0833]

[0834] In the general formulas (D-32) to (D-37), X1 to X6 are independently oxygen atoms, sulfur atoms, or CR atoms, respectively. 151 R 152 ,

[0835] By R 151 and R 152 The group

[0836] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[0837] They bond to each other to form substituted or unsubstituted fused rings.

[0838] By R 201 ~R 210 One or more groups consisting of two or more adjacent elements.

[0839] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[0840] They bond to each other to form substituted or unsubstituted fused rings.

[0841] By R 211 ~R 220 One or more groups consisting of two or more adjacent elements.

[0842] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[0843] They bond to each other to form substituted or unsubstituted fused rings.

[0844] By R 221 ~R 230 One or more groups consisting of two or more adjacent elements.

[0845] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[0846] They bond to each other to form substituted or unsubstituted fused rings.

[0847] By R 231 ~R 240 One or more groups consisting of two or more adjacent elements.

[0848] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[0849] They bond to each other to form substituted or unsubstituted fused rings.

[0850] By R 241 ~R 250 One or more groups consisting of two or more adjacent elements.

[0851] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[0852] They bond to each other to form substituted or unsubstituted fused rings.

[0853] By R 251 ~R 260 One or more groups consisting of two or more adjacent elements.

[0854] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[0855] They bond to each other to form substituted or unsubstituted fused rings.

[0856] R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 151 R 152 and R201 ~R 260 Each independently

[0857] hydrogen atom,

[0858] Halogen atoms,

[0859] substituted or unsubstituted aryl groups with 6 to 14 carbon atoms

[0860] Substituted or unsubstituted heterocyclic groups with 5 to 14 cyclic atoms

[0861] Substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms

[0862] Substituted or unsubstituted alkyl halides with 1 to 6 carbon atoms

[0863] Substituted or unsubstituted cycloalkyl groups with 3 to 30 carbon atoms

[0864] Substituted or unsubstituted alkylsilyl groups having 3 to 6 carbon atoms

[0865] hydroxyl,

[0866] Substituted or unsubstituted alkoxy groups having 1 to 6 carbon atoms

[0867] Substituted or unsubstituted haloalkoxy groups having 1 to 6 carbon atoms

[0868] Substituted or unsubstituted aryloxy groups with 6 to 14 carbon atoms,

[0869] substituted or unsubstituted arylamino groups with 6 to 28 carbon atoms in the cyclic formation,

[0870] Substituted or unsubstituted alkylamino groups with 2 to 12 carbon atoms

[0871] Thiol group,

[0872] Substituted or unsubstituted alkylthio groups having 1 to 6 carbon atoms, or

[0873] Arylthio groups, substituted or unsubstituted, with 6 to 14 carbon atoms in the cyclic group.

[0874] * indicates the site where the carbon atom of the six-membered ring in the general formula (2) is bonded.

[0875] In the general formula (2), R is preferably used as a substituent. 201 ~R 260 Each of the following can be independently a halogen atom, an unsubstituted aryl group having 6 to 14 carbon atoms, an unsubstituted heterocyclic group having 5 to 14 carbon atoms, or an unsubstituted alkyl group having 1 to 6 carbon atoms.

[0876] R as a substituent 151 and R 152Each is independently an unsubstituted aryl group having 6 to 14 carbon atoms in a cyclic ring, or an unsubstituted alkyl group having 1 to 6 carbon atoms.

[0877] In compound M2, R is more preferably a substituent. 201 ~R 260 They are, independently, an unsubstituted aryl group having 6 to 14 carbon atoms, an unsubstituted heterocyclic group having 5 to 14 carbon atoms, or an unsubstituted alkyl group having 1 to 6 carbon atoms.

[0878] R as a substituent 151 and R 152 Each is independently an unsubstituted aryl group having 6 to 14 carbon atoms in a cyclic ring, or an unsubstituted alkyl group having 1 to 6 carbon atoms.

[0879] In the general formula (2), R is also preferred. 201 ~R 260 It is a hydrogen atom.

[0880] R as a substituent 151 and R 152 Each is independently an unsubstituted aryl group having 6 to 14 carbon atoms in a cyclic ring, or an unsubstituted alkyl group having 1 to 6 carbon atoms.

[0881] Compounds represented by general formula (22)

[0882] [Chemistry 37]

[0883]

[0884] In the general formula (22), Ar1 is any group selected from the group consisting of substituted or unsubstituted aryl groups with 6 to 30 cyclic carbon atoms, substituted or unsubstituted heteroaryl groups with 5 to 30 cyclic carbon atoms, substituted or unsubstituted alkyl groups with 1 to 30 cyclic carbon atoms, substituted or unsubstituted fluoroalkyl groups with 1 to 30 cyclic carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 30 cyclic carbon atoms, substituted or unsubstituted aralkyl groups with 7 to 30 cyclic carbon atoms, substituted phosphoryl groups, substituted silyl groups, cyano groups, nitro groups, carboxyl groups, and groups represented by the following general formulas (1a) to (1j).

[0885] Ar EWG It is a heteroaryl group with 5 to 30 cyclic atoms containing one or more nitrogen atoms in the ring, or an aryl group with 6 to 30 cyclic carbons substituted with one or more cyano groups.

[0886] Ar X Ar can be either a hydrogen atom or a substituent, and can be a substituent. XIt is any group selected from the group consisting of substituted or unsubstituted aryl groups having 6 to 30 cyclic carbon atoms, substituted or unsubstituted heteroaryl groups having 5 to 30 cyclic carbon atoms, substituted or unsubstituted alkyl groups having 1 to 30 cyclic carbon atoms, substituted or unsubstituted fluoroalkyl groups having 1 to 30 cyclic carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 30 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 cyclic carbon atoms, substituted phosphoryl groups, substituted silyl groups, cyano groups, nitro groups, carboxyl groups, and groups represented by the following general formulas (1a) to (1j).

[0887] n is 0, 1, 2, 3, 4, or 5. When n is 2, 3, 4, or 5, multiple Ar... X Whether they are the same or different,

[0888] Ring (A) is a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring, wherein ring (A) is a five-membered, six-membered, or seven-membered ring, Ar EWG Ar1 and Ar X They bond to the elements that make up the ring (A),

[0889] Ar1 and Ar X At least one of them is any group selected from the group consisting of groups represented by the following general formulas (1a) to (1j).

[0890] [Chemistry 38]

[0891]

[0892] [Chemistry 39]

[0893]

[0894] [Chemistry 40]

[0895]

[0896] (In the general formulas (1a) to (1j), X1 to X 20 Each is independently a nitrogen atom (N) or with R. A1 bonded carbon atoms (CR) A1 ),

[0897] In the general formula (1b), any one of X5 to X8 is related to X9 to X 12 Any one of the bonded carbon atoms in X9~X 12 Each of the atoms in the matrix is ​​a carbon atom bonded to any one of X5 to X8.

[0898] In the general formula (1c), any one of X5 to X8 is a carbon atom bonded to a nitrogen atom in a ring containing A2.

[0899] In the general formula (1e), X5~X8 and X 18 Any one of them is related to X9~X 12 Any one of the bonded carbon atoms in X9~X 12 Any one of them is related to X5~X8 and X 18 Any one of the bonded carbon atoms in it,

[0900] In the general formula (1f), X5~X8 and X 18 Any one of them is related to X9~X 12 and X 19 Any one of the bonded carbon atoms in X9~X 12 and X 19 Any one of them is related to X5~X8 and X 18 Any one of the bonded carbon atoms in it,

[0901] In the general formula (1g), any one of X5 to X8 is related to X9 to X... 12 and X 19 Any one of the bonded carbon atoms in X9~X 12 and X 19 Each of the atoms in the matrix is ​​a carbon atom bonded to any one of X5 to X8.

[0902] In the general formula (1h), X5~X8 and X 18 Each of them is a carbon atom bonded to a nitrogen atom in a ring containing A2.

[0903] In the general formula (1i), X5~X8 and X 18 Any one of them is included in X9~X 12 and X 19 The ring and containing X 13 ~X 16 and X 20 The ring-linked nitrogen atom is bonded to the carbon atom.

[0904] In the general formula (1j), any one of X5 to X8 is a combination of X9 to X... 12 and X 19 The ring and containing X 13 ~X 16 and X 20 The ring-linked nitrogen atom is bonded to the carbon atom.

[0905] Composed of multiple R A1 One or more groups consisting of two or more adjacent elements.

[0906] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[0907] They bond to each other to form substituted or unsubstituted fused rings.

[0908] R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. A1 Each independently

[0909] Any group selected from the group consisting of hydrogen atoms, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups with 5 to 30 carbon atoms, substituted or unsubstituted alkyl groups with 1 to 30 carbon atoms, substituted or unsubstituted fluoroalkyl groups with 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 30 carbon atoms, substituted or unsubstituted aralkyl groups with 7 to 30 carbon atoms, substituted phosphoryl groups, substituted silyl groups, cyano groups, nitro groups, and carboxyl groups.

[0910] Multiple R A1 They are the same or different from each other.

[0911] In the general formulas (1a) to (1j), * indicates the site bonded to the ring (A).

[0912] In the general formulas (1a) to (1j), A1 and A2 are independently a single bond, an oxygen atom (O), a sulfur atom (S), and a C(R) atom, respectively. 2021 (R) 2022 ), Si(R) 2023 (R) 2024 C (=O), S (=O), SO2, or N (R) 2025 R 2021 ~R 2025 R can be a hydrogen atom or a substituent, and can be a substituent. 2021 ~R 2025 Each and every one of the following groups can be independently selected from the group consisting of substituted or unsubstituted aryl groups with 6 to 30 cyclic carbon atoms, substituted or unsubstituted heteroaryl groups with 5 to 30 cyclic carbon atoms, substituted or unsubstituted alkyl groups with 1 to 30 cyclic carbon atoms, substituted or unsubstituted fluoroalkyl groups with 1 to 30 cyclic carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 30 cyclic carbon atoms, substituted or unsubstituted aralkyl groups with 7 to 30 cyclic carbon atoms, substituted phosphoryl groups, substituted silyl groups, cyano groups, nitro groups, and carboxyl groups.

[0913] In the general formulas (1a) to (1j), Ara is any group selected from the group consisting of substituted or unsubstituted aryl groups having 6 to 30 cyclic carbon atoms, substituted or unsubstituted heteroaryl groups having 5 to 30 cyclic carbon atoms, substituted or unsubstituted alkyl groups having 1 to 30 cyclic carbon atoms, substituted or unsubstituted fluoroalkyl groups having 1 to 30 cyclic carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 30 cyclic carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 cyclic carbon atoms, substituted phosphoryl groups, and substituted silyl groups.

[0914] In the general formula (1a), X1 to X8 are related to R A1 bonded carbon atoms (CR) A1 In the case of ), multiple R are preferred. A1 It does not form a ring.

[0915] The preferred form of Ara is an aryl group with 6 to 30 cyclic carbon atoms (substituted or unsubstituted) or a heteroaryl group with 5 to 30 cyclic atoms (substituted or unsubstituted).

[0916] The general formula (1a) is represented by the following general formula (1aa) when A1 is a single bond, by the following general formula (1ab) when A1 is O, by the following general formula (1ac) when A1 is S, and by the following general formula (1ac) when A1 is C(R) 2021 (R) 2022 In the case of ), it is expressed by the following general formula (1ad), where A1 is Si(R) 2023 (R) 2024 In the case of A1 being C (=O), it is represented by the following general formula (1ae); in the case of A1 being S (=O), it is represented by the following general formula (1ag); in the case of A1 being SO2, it is represented by the following general formula (1ah); in the case of A1 being N (R 2025 In the case of ), it is represented by the following general formula (1ai). In these following general formulas (1aa) to (1ai), X1 to X8 and R 2021 ~R 2025 Synonymous with the above. Regarding the general formulas (1b), (1c), (1e), (1g) to (1j), the connection method between the rings based on A1 and A2 is also the same as in the following general formulas (1aa) to (1ai). In the following general formula (1aa), X1 to X8 are connected to R... A1 bonded carbon atoms (CR) A1 In the case of ), it is preferred that multiple Rs be used as substituents. A1 It does not form a ring.

[0917] [Chemistry 41]

[0918]

[0919] [Chemistry 42]

[0920]

[0921] [Chemistry 43]

[0922]

[0923] The first sensitizing material of this embodiment is preferably represented by the following general formula (221).

[0924] [Chemistry 44]

[0925]

[0926] In the general formula (221), Ar1 and Ar EWG Ar x , n and ring (A) are respectively related to Ar1, Ar in the general formula (22) EWG Ar x Synonyms for n and ring (A).

[0927] In one embodiment of this invention, the first sensitizing material is a compound represented by the following general formula (222).

[0928] [Chemistry 45]

[0929]

[0930] In the general formula (222), Y1 to Y5 are independently nitrogen atoms (N), carbon atoms bonded to cyano groups (C-CN), or atoms bonded to R. A2 bonded carbon atoms (CR) A2 At least one of Y1 to Y5 is N or C-CN. Multiple R A2 They are the same or different from each other.

[0931] Composed of multiple R A2 One or more groups consisting of two or more adjacent elements.

[0932] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[0933] They bond to each other to form substituted or unsubstituted fused rings.

[0934] R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. A2 Each group is independently selected from the group consisting of hydrogen atoms, substituted or unsubstituted aryl groups with 6 to 30 cyclic carbon atoms, substituted or unsubstituted heteroaryl groups with 5 to 30 cyclic carbon atoms, substituted or unsubstituted alkyl groups with 1 to 30 cyclic carbon atoms, substituted or unsubstituted fluoroalkyl groups with 1 to 30 cyclic carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 30 cyclic carbon atoms, substituted or unsubstituted aralkyl groups with 7 to 30 cyclic carbon atoms, substituted phosphoryl groups, substituted silyl groups, cyano groups, nitro groups, and carboxyl groups.

[0935] Multiple R A2 They are the same or different from each other.

[0936] In the general formula (222), Ar1 is synonymous with Ar1 in the general formula (22).

[0937] In the general formula (222), Ar2 to Ar5 are each independently a hydrogen atom or a substituent, and Ar2 to Ar5 as substituents are each independently selected from the group consisting of substituted or unsubstituted aryl groups with 6 to 30 cyclic carbon atoms, substituted or unsubstituted heteroaryl groups with 5 to 30 cyclic carbon atoms, substituted or unsubstituted alkyl groups with 1 to 30 cyclic carbon atoms, substituted or unsubstituted fluoroalkyl groups with 1 to 30 cyclic carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 30 cyclic carbon atoms, substituted or unsubstituted aralkyl groups with 7 to 30 cyclic carbon atoms, substituted phosphoryl groups, substituted silyl groups, cyano groups, nitro groups, carboxyl groups, and groups represented by the general formulas (1a) to (1c).

[0938] In the general formula (222), if any one or more of Ar2 to Ar5 is a hydrogen atom, it is preferred that all of the hydrogen atoms are protium atoms, or at least one of the hydrogen atoms is a deuterium atom, or all of the hydrogen atoms are deuterium atoms.

[0939] In the general formula (222), if any one or more of Ar2 to Ar5 is a substituent and the substituent has one or more hydrogen atoms, it is preferred that all the hydrogen atoms are protium atoms, or at least one of the hydrogen atoms is deuterium atom, or all the hydrogen atoms are deuterium atoms.

[0940] In the general formula (222), at least one of Ar1 to Ar5 is any group selected from the group consisting of groups represented by the general formulas (1a) to (1c).

[0941] In one embodiment of this invention, the first sensitizing material is a compound represented by the following general formula (11aa), the following general formula (11bb), or the following general formula (11cc).

[0942] [Chemistry 46]

[0943]

[0944] [Chemistry 47]

[0945]

[0946] In the general formulas (11aa), (11bb), and (11cc), Y1~Y5, R A2 Ar2~Ar5, X1~X 16 R A1 , and Ara respectively represent Y1~Y5, R above. A2 Ar2~Ar5, X1~X 16 R A1 It has the same meaning as Ara.

[0947] In one embodiment of this invention, the first sensitizing material is, for example, a compound represented by the following general formula (23).

[0948] [Chemistry 48]

[0949]

[0950] In the general formula (23),

[0951] Az is from

[0952] Composed of substituted or unsubstituted pyridine rings,

[0953] Substituted or unsubstituted pyrimidine rings

[0954] Substituted or unsubstituted triazine rings, and

[0955] Substituted or unsubstituted pyrazine ring

[0956] The selected ring structure in the group.

[0957] c is 0, 1, 2, 3, 4, or 5.

[0958] When c is 0, Cz and Az are bonded by a single bond.

[0959] When c is 1, 2, 3, 4 or 5, L 23 From

[0960] Composed or unsubstituted arylene groups with 6 to 30 carbon atoms, and

[0961] Substituted or unsubstituted heteroaryl groups with 5 to 30 cyclic atoms

[0962] The linking groups selected from the constituent groups,

[0963] When c is 2, 3, 4, or 5, multiple L 23 Whether they are the same or different,

[0964] Multiple L 23 They may or may not bond together to form a ring.

[0965] Cz is represented by the following general formula (23a).

[0966] [Chemistry 49]

[0967]

[0968] In the general formula (23a),

[0969] Y 21 To Y 28 Each independently consists of a nitrogen atom or CR A3 ,

[0970] Composed of multiple R A3 One or more groups consisting of two or more adjacent elements.

[0971] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[0972] They bond to each other to form substituted or unsubstituted fused rings.

[0973] R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. A3 Each independently from

[0974] Composed of hydrogen atoms,

[0975] substituted or unsubstituted aryl groups with 6 to 30 carbon atoms

[0976] Substituted or unsubstituted heteroaryl groups with 5 to 30 cyclic atoms

[0977] Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms

[0978] Substituted or unsubstituted fluoroalkyl groups with 1 to 30 carbon atoms

[0979] Substituted or unsubstituted cycloalkyl groups with 3 to 30 carbon atoms

[0980] Aryl groups with 7 to 30 carbon atoms, substituted or unsubstituted

[0981] Substituted phosphoryl group,

[0982] Replacement of silyl groups

[0983] cyano,

[0984] Nitro, and

[0985] carboxyl

[0986] The groups selected from the group that constitute the composition,

[0987] Multiple R A3 Whether they are the same or different,

[0988] *1 indicates that L 23 The carbon atom bonding sites in the structure of the connecting group shown, or the carbon atom bonding sites in the ring structure shown in Az.

[0989] Y is also preferred 21 To Y 28 For CR A3 .

[0990] Preferably, c in the general formula (23) is 0 or 1.

[0991] It is also preferred that the Cz be represented by the following general formula (23b), general formula (23c) or general formula (23d).

[0992] [Transformation 50]

[0993]

[0994] [Chemistry 51]

[0995]

[0996] [Chemistry 52]

[0997]

[0998] In the general formulas (23b), (23c), and (23d), Y 21 To Y 28 and Y 51 To Y 58 Each independently consists of a nitrogen atom or CR A4 ,

[0999] In the general formula (23b), Y 25 To Y 28 At least one of them is with Y 51 To Y 54 Any one of the bonded carbon atoms in Y 51 To Y 54 At least one of them is with Y 25 To Y 28 Any one of the bonded carbon atoms in it,

[1000] In the general formula (23c), Y 25 To Y 28 At least one of them is with Y 51 To Y 58 In a nitrogen-containing fused ring, the nitrogen atom is bonded to the carbon atom.

[1001] In the general formula (23d), *a and *b respectively represent the relationship between Y and Y. 21 To Y 28 Any bonded site in Y 25 To Y 28 At least one of them is the bonding site shown in *a, Y 25 To Y 28 At least one of them is the bonding site shown in *b.

[1002] n is 1, 2, 3, or 4.

[1003] Composed of multiple R A4 One or more groups consisting of two or more adjacent elements.

[1004] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[1005] They bond to each other to form substituted or unsubstituted fused rings.

[1006] R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. A4 Each independently from

[1007] Composed of hydrogen atoms,

[1008] substituted or unsubstituted aryl groups with 6 to 30 carbon atoms

[1009] Substituted or unsubstituted heteroaryl groups with 5 to 30 cyclic atoms

[1010] Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms

[1011] Substituted or unsubstituted fluoroalkyl groups with 1 to 30 carbon atoms

[1012] Substituted or unsubstituted cycloalkyl groups with 3 to 30 carbon atoms

[1013] Aryl groups, substituted or unsubstituted, having 7 to 30 carbon atoms

[1014] Substituted phosphoryl group,

[1015] Replacement of silyl groups

[1016] cyano,

[1017] Nitro, and

[1018] carboxyl

[1019] Any substituent selected from the group that constitutes the composition,

[1020] Multiple R A4 Whether they are the same or different,

[1021] Z 21 and Z 21 Each independently consists of oxygen atoms, sulfur atoms, and NR. 45 and CR 46 R 47 Choose any one from the groups formed.

[1022] By R 46 and R 47 The group

[1023] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[1024] They bond to each other to form substituted or unsubstituted fused rings.

[1025] R 45 R, and R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 46 and R 47 Each independently from

[1026] Composed of hydrogen atoms,

[1027] substituted or unsubstituted aryl groups with 6 to 30 carbon atoms

[1028] Substituted or unsubstituted heteroaryl groups with 5 to 30 cyclic atoms

[1029] Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms

[1030] Substituted or unsubstituted fluoroalkyl groups with 1 to 30 carbon atoms

[1031] Substituted or unsubstituted cycloalkyl groups with 3 to 30 carbon atoms

[1032] Aryl groups, substituted or unsubstituted, having 7 to 30 carbon atoms

[1033] Substituted phosphoryl group,

[1034] Replacement of silyl groups

[1035] cyano,

[1036] Nitro, and

[1037] carboxyl

[1038] Any substituent selected from the group that constitutes the composition,

[1039] Multiple R 45 Whether they are the same or different,

[1040] Multiple R 46 Whether they are the same or different,

[1041] Multiple R 47 Whether they are the same or different,

[1042] * indicates the site where the carbon atom is bonded to the ring structure shown in Az.

[1043] Z is preferred 21 For NR 45 .

[1044] In Z 21 For NR 45 In the case of R, it is preferred 45 Aryl groups with 6 to 30 carbon atoms, either substituted or unsubstituted.

[1045] Z is preferred 22 For NR45 .

[1046] In Z 22 For NR 45 In the case of R, it is preferred 45 Aryl groups with 6 to 30 carbon atoms, either substituted or unsubstituted.

[1047] Preferred Y 51 To Y 58 For CR A4 In this case, Y 51 To Y 58 At least one of them is a carbon atom bonded to the ring structure shown in the general formula (23a).

[1048] It is also preferred that Cz is represented by the general formula (23d) and n is 1.

[1049] Preferably, Az is a ring structure selected from the group consisting of substituted or unsubstituted pyrimidine rings and substituted or unsubstituted triazine rings.

[1050] Az is a ring structure selected from the group consisting of a pyrimidine ring having a substituent and a triazine ring having a substituent, wherein the substituents of the pyrimidine ring and the triazine ring are more preferably selected from the group consisting of an aryl group having 6 to 30 cyclic carbon atoms (substituted or unsubstituted) and a heteroaryl group having 5 to 30 cyclic carbon atoms (substituted or unsubstituted), and even more preferably an aryl group having 6 to 30 cyclic carbon atoms (substituted or unsubstituted).

[1051] When the pyrimidine ring and triazine ring of Az have substituted or unsubstituted aryl groups as substituents, the number of carbon atoms in the cyclization of the aryl group is preferably 6 to 20, more preferably 6 to 14, and even more preferably 6 to 12.

[1052] When Az has a substituted or unsubstituted aryl group as a substituent, the substituent is preferably any substituent selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted terphenyl and substituted or unsubstituted fluorenyl, more preferably any substituent selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl and substituted or unsubstituted naphthyl.

[1053] When Az has a substituted or unsubstituted heteroaryl group as a substituent, the substituent is preferably any substituent selected from the group consisting of a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuran group, and a substituted or unsubstituted dibenzothiophene group.

[1054] R A4 Each can be an independent hydrogen atom or a substituent, with R preferably being a substituent. A4It is any substituent selected from the group consisting of aryl groups with 6 to 30 cyclic carbon atoms (substituted or unsubstituted) and heteroaryl groups with 5 to 30 cyclic atoms (substituted or unsubstituted).

[1055] R as a substituent A4 In the case of a substituted or unsubstituted aryl group with 6 to 30 carbon atoms in the cyclic group, R as a substituent A4 Preferably, it is any substituent selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted terphenyl and substituted or unsubstituted fluorenyl, more preferably any substituent selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl and substituted or unsubstituted naphthyl.

[1056] R as a substituent A4 In the case of a heteroaryl group with 5 to 30 cyclic atoms, either substituted or unsubstituted, R as a substituent A4 Preferably, it is any substituent selected from the group consisting of substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl and substituted or unsubstituted dibenzothiophenel.

[1057] R is preferred as a substituent 45 R 46 and R 47 Each of the following is a substituent selected independently from the group consisting of aryl groups with 6 to 30 cyclic carbon atoms (substituted or unsubstituted), heteroaryl groups with 5 to 30 cyclic carbon atoms (substituted or unsubstituted), and alkyl groups with 1 to 30 cyclic carbon atoms (substituted or unsubstituted).

[1058] • Method for manufacturing the first sensitizing material

[1059] The first sensitizing material can be manufactured using known methods.

[1060] Specific examples of the first sensitizing material (a compound represented by the general formula (2) or the general formula (22)) in this embodiment may include the following compounds. However, the first sensitizing material is not limited to these specific examples of compounds.

[1061] [Chemistry 53]

[1062]

[1063] [Chemistry 54]

[1064]

[1065] [Chemistry 55]

[1066]

[1067] [Chemistry 56]

[1068]

[1069] [Chemistry 57]

[1070]

[1071] [Chem.58]

[1072]

[1073] [Chemistry 59]

[1074]

[1075] [Transformation 60]

[1076]

[1077] [Chemistry 61]

[1078]

[1079] [Chemistry 62]

[1080]

[1081] [Chemistry 63]

[1082]

[1083] [Chemistry 64]

[1084]

[1085] In one embodiment of this invention, the first sensitizing material is a compound represented by any one of the following general formulas (11) to (13).

[1086] [Chemistry 65]

[1087]

[1088] In the general formulas (11) to (13), R1 to R4 are each independently any one of the groups represented by the general formulas (1-1) to (1-6) below, or any one of the groups represented by the general formulas (2-1) to (2-4) below, wherein at least one of R1 to R4 is any one of the groups represented by the general formulas (1-1) to (1-6) below, and at least one of R1 to R4 is any one of the groups represented by the general formulas (2-1) to (2-4) below.

[1089] [Chemistry 66]

[1090]

[1091] In the general formula (1-1), X1 is an oxygen atom, a sulfur atom, or a CR atom. 151 R 152 R 101 ~R 110 Each can be a hydrogen atom or a substituent, R. 151 and R 152 Each is independently a hydrogen atom or a substituent, or R 151 and R 152 They bond together to form a ring.

[1092] R as a substituent 101 ~R 110 R 151 and R 152 Each independently

[1093] substituted or unsubstituted aryl groups with 6 to 14 carbon atoms

[1094] Substituted or unsubstituted heterocyclic groups with 5 to 14 cyclic atoms

[1095] Substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms

[1096] Substituted or unsubstituted alkylsilyl groups having 3 to 6 carbon atoms

[1097] Substituted or unsubstituted alkoxy groups having 1 to 6 carbon atoms

[1098] Substituted or unsubstituted aryloxy groups with 6 to 14 carbon atoms,

[1099] Substituted or unsubstituted alkylamino groups with 2 to 12 carbon atoms

[1100] Substituted or unsubstituted alkylthio groups having 1 to 6 carbon atoms, or

[1101] Arylthio groups with 6 to 14 carbon atoms, either substituted or unsubstituted.

[1102] In the general formula (1-2), X2 and R 111 ~R 120 respectively with X1 and R in the general formula (1-1) 101 ~R 110 Synonyms.

[1103] In the general formula (1-3), X3 and R 121 ~R 130 respectively with X1 and R in the general formula (1-1) 101 ~R 110 Synonyms.

[1104] In the general formula (1-4), X4 and R 131 ~R 140 respectively with X1 and R in the general formula (1-1) 101 ~R 110 Synonyms.

[1105] In the general formula (1-5), X5 and R 141 ~R 150 respectively with X1 and R in the general formula (1-1) 101 ~R 110 Synonyms.

[1106] In the general formula (1-6), X6 and R 61 ~R 70 respectively with X1 and R in the general formula (1-1) 101 ~R 110 Synonyms. * Represents the sites where carbon atoms of the benzene ring in the general formulas (11) to (13) are bonded independently.

[1107] In the general formulas (1-1) to (1-6), in R 101 ~R 110 R 111 ~R 120 R 121 ~R 130 R 131 ~R 140 R 141 ~R 150 R 61 ~R 70 R 151 and R 152 When any one or more of the atoms are hydrogen atoms, it is preferable that all of the hydrogen atoms are protium, or that any one or more of the hydrogen atoms are deuterium, or that all of the hydrogen atoms are deuterium.

[1108] In the general formulas (1-1) to (1-6), in R 101 ~R 110 R 111 ~R 120 R 121 ~R 130 R 131 ~R 140 R 141 ~R 150 R 61 ~R 70 R 151 and R 152When any one or more of the substituents are substituents and the substituents have one or more hydrogen atoms, it is preferable that all the hydrogen atoms are protium, or that any one or more of the hydrogen atoms are deuterium, or that all the hydrogen atoms are deuterium.

[1109] [Chemistry 67]

[1110]

[1111] In the general formula (2-1), R 161 ~R 168 Each can be an independent hydrogen atom or a substituent.

[1112] Halogen atoms,

[1113] R as a substituent 161 ~R 168 Each independently

[1114] substituted or unsubstituted aryl groups with 6 to 14 carbon atoms

[1115] Substituted or unsubstituted heterocyclic groups with 5 to 14 cyclic atoms

[1116] Substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms

[1117] Substituted or unsubstituted alkyl halides with 1 to 30 carbon atoms

[1118] Substituted or unsubstituted alkylsilyl groups having 3 to 6 carbon atoms

[1119] Substituted or unsubstituted alkoxy groups having 1 to 6 carbon atoms

[1120] Substituted or unsubstituted aryloxy groups with 6 to 14 carbon atoms,

[1121] Substituted or unsubstituted alkylamino groups with 2 to 12 carbon atoms

[1122] Substituted or unsubstituted alkylthio groups having 1 to 6 carbon atoms, or

[1123] Arylthio groups with 6 to 14 carbon atoms, either substituted or unsubstituted.

[1124] In the general formula (2-2), R 171 ~R 180 R can be a hydrogen atom or a substituent, and can be a substituent. 171 ~R 180 Independently related to R in the general formula (2-1) 161 ~R 168 The listed substituents are synonyms.

[1125] In the general formula (2-3), R 181~R 190 R can be a hydrogen atom or a substituent, and can be a substituent. 181 ~R 190 Independently related to R in the general formula (2-1) 161 ~R 168 The listed substituents are synonyms.

[1126] In the general formula (2-4), R 191 ~R 200 R can be a hydrogen atom or a substituent, and can be a substituent. 191 ~R 200 Independently related to R in the general formula (2-1) 161 ~R 168 The exemplified substituents are synonymous. *Indicates independently the sites where the carbon atoms of the benzene ring in the general formulas (11) to (13) are bonded.

[1127] In the general formulas (2-1) to (2-4), in R 161 ~R 168 R 171 ~R 180 R 181 ~R 190 and R 191 ~R 200 When any one or more of the atoms are hydrogen atoms, it is preferable that all of the hydrogen atoms are protium, or that any one or more of the hydrogen atoms are deuterium, or that all of the hydrogen atoms are deuterium.

[1128] In the general formulas (2-1) to (2-4), in R 161 ~R 168 R 171 ~R 180 R 181 ~R 190 and R 191 ~R 200 When any one or more of the substituents are substituents and the substituents have one or more hydrogen atoms, it is preferable that all the hydrogen atoms are protium, or that any one or more of the hydrogen atoms are deuterium, or that all the hydrogen atoms are deuterium.

[1129] In the first sensitizing material of this embodiment, when multiple groups represented by the general formula (1-1) are present as groups R1 to R4, it is preferable that the multiple groups represented by the general formula (1-1) are identical groups including substituents.

[1130] When multiple groups represented by the general formula (1-2) are present as groups R1 to R4, it is preferable that the multiple groups represented by the general formula (1-2) are identical to each other, including the substituents.

[1131] When multiple groups represented by the general formula (1-3) are present as groups R1 to R4, it is preferable that the multiple groups represented by the general formula (1-3) are identical to each other, including the substituents.

[1132] When multiple groups represented by the general formulas (1-4) are present as groups R1 to R4, it is preferable that the multiple groups represented by the general formulas (1-4) are identical to each other, including the substituents.

[1133] When multiple groups represented by the general formulas (1-5) are present as groups R1 to R4, it is preferable that the multiple groups represented by the general formulas (1-5) are identical to each other, including the substituents.

[1134] When multiple groups represented by the general formulas (1-6) are present as groups R1 to R4, it is preferable that the multiple groups represented by the general formulas (1-6) are identical to each other, including the substituents.

[1135] Specifically, for example, when selecting two groups represented by the general formula (1-1) as groups R1 and R2, selecting one group represented by the general formula (1-2) as group R3, and selecting one group represented by the general formula (2-1) as group R4, it is preferable that the two groups represented by the general formula (1-1) (groups R1 and R2) are identical to each other, including substituents.

[1136] Furthermore, for example, when three groups represented by the general formula (1-1) are selected as groups R1 to R3, it is preferable that the three groups represented by the general formula (1-1) (groups R1 to R3) are the same as each other, including substituents.

[1137] In one embodiment, when two of R1 to R4 are selected from groups represented by general formulas (1-1) to (1-6), and the remaining two are selected from groups represented by general formulas (2-1) to (2-4), it is preferable that the two groups represented by general formulas (1-1) to (1-6) are both represented by one of the general formulas (1-1) to (1-6) and are the same groups including substituents.

[1138] Furthermore, when three of R1 to R4 are selected from groups represented by the general formulas (1-1) to (1-6), and the remaining one is selected from groups represented by the general formulas (2-1) to (2-4), it is preferable that the three groups represented by the general formulas (1-1) to (1-6) are all represented by one of the general formulas (1-1) to (1-6) and are groups that are identical to each other, including substituents.

[1139] For example, when selecting three groups represented by general formula (1-1) as groups R1 to R4, it is preferable that the three selected groups are groups represented by general formula (1-1) and are the same as each other, including substituents.

[1140] In one embodiment of this invention, when multiple groups represented by the general formula (2-1) are used as groups R1 to R4, it is preferable that the multiple groups represented by the general formula (2-1) are identical to each other, including substituents.

[1141] When multiple groups represented by the general formula (2-2) are present as groups R1 to R4, it is preferable that the multiple groups represented by the general formula (2-2) are identical to each other, including the substituents.

[1142] When multiple groups represented by the general formula (2-3) are present as groups R1 to R4, it is preferable that the multiple groups represented by the general formula (2-3) are identical to each other, including the substituents.

[1143] When multiple groups represented by the general formula (2-4) are present as groups R1 to R4, it is preferable that the multiple groups represented by the general formula (2-4) are identical to each other, including the substituents.

[1144] Specifically, for example, when selecting two groups represented by the general formula (2-1) as groups R1 and R2, selecting one group represented by the general formula (2-2) as group R3, and selecting one group represented by the general formula (1-1) as group R4, it is preferable that the two groups represented by the general formula (2-1) (groups R1 and R2) are identical to each other, including substituents.

[1145] Furthermore, for example, when three groups represented by the general formula (2-1) are selected as groups R1 to R3, it is preferable that the three groups represented by the general formula (2-1) (groups R1 to R3) are the same as each other, including substituents.

[1146] In one embodiment, when two of R1 to R4 are selected from groups represented by general formulas (2-1) to (2-4), and the remaining two are selected from groups represented by general formulas (1-1) to (1-6), it is preferable that the two groups represented by general formulas (2-1) to (2-4) are both represented by one of the general formulas (2-1) to (2-4) and are the same as each other, including substituents.

[1147] Furthermore, when three of R1 to R4 are selected from groups represented by the general formulas (2-1) to (2-4), and the remaining one is selected from groups represented by the general formulas (1-1) to (1-6), it is preferable that the three groups represented by the general formulas (2-1) to (2-4) are all represented by one of the general formulas (2-1) to (2-4) and are groups that are identical to each other, including substituents.

[1148] For example, when selecting three groups represented by general formula (2-1) as groups R1 to R4, it is preferable that the three selected groups are groups represented by general formula (2-1) and are the same as each other, including substituents.

[1149] In one embodiment of this invention, the first sensitizing material is any one of the compounds represented by the following general formulas (101) to (123).

[1150] [Chemistry 68]

[1151]

[1152] [Chemistry 69]

[1153]

[1154] [Chemistry 70]

[1155]

[1156] In the general formulas (101) to (123), D1 is independently any one of the groups represented by the general formulas (1-1) to (1-6), and D2 is independently any one of the groups represented by the general formulas (2-1) to (2-4). Multiple D1s may be the same or different from each other, and multiple D2s may be the same or different from each other.

[1157] In one embodiment of this invention, it is preferred that D1 in the general formulas (101) to (123) are the same group.

[1158] In one embodiment of this invention, it is preferred that D2 in the general formulas (101) to (123) are the same group as each other.

[1159] That is, in one embodiment of this invention, it is more preferable that D1 in the general formulas (101) to (123) are the same group and D2 are the same group.

[1160] In one embodiment of this invention, the first sensitizing material is preferably any one of the compounds represented by the general formulas (101), (106), (107), (110), (111), and (116) to (119).

[1161] In the general formulas (1-1) to (1-6), X1 to X6 are preferably oxygen atoms.

[1162] In the general formulas (1-1) to (1-6), X1 to X6 are preferably sulfur atoms.

[1163] In the general formulas (1-1) to (1-6), X1 to X6 are preferably CR. 151 R 152 .

[1164] In one embodiment of this invention, the group represented by general formulas (1-1) to (1-6) is preferably a group represented by general formula (1-1), a group represented by general formula (1-2), or a group represented by general formula (1-4).

[1165] In one embodiment of this invention, it is preferred that the group represented by general formulas (2-1) to (2-4) is any one of the groups represented by general formulas (2-5) to (2-14) and the following general formulas (2-15) to (2-17).

[1166] [Chemistry 71]

[1167]

[1168] In the general formulas (2-5) to (2-17), * independently represents the site where the carbon atom of the benzene ring in the general formulas (11) to (13) is bonded, and D represents deuterium.

[1169] In one embodiment of this invention, the groups represented by general formulas (2-1) to (2-4) are groups represented by general formula (2-2), groups represented by general formula (2-3), or groups represented by general formula (2-4).

[1170] In one embodiment of this invention, it is also preferred that the groups represented by general formulas (2-1) to (2-4) are all groups represented by general formula (2-1).

[1171] In one embodiment of this invention, the group represented by the general formula (2-1) is either the group represented by the general formula (2-5) or the group represented by the general formula (2-15).

[1172] In one embodiment of this invention, when the first sensitizing material has a group represented by the general formula (2-1), R 161 ~R 168 Each independently

[1173] hydrogen atom,

[1174] Substituted or unsubstituted aryl groups with 6 to 14 carbon atoms, or

[1175] Alkyl groups with 1 to 6 carbon atoms, whether substituted or unsubstituted.

[1176] In one embodiment of this invention, when the first sensitizing material has a group represented by the general formula (2-1), R 161 R 163 R 166 and R 168 At least one of them has a substituent.

[1177] The substituents are independently...

[1178] Substituted or unsubstituted aryl groups with 6 to 14 carbon atoms, or

[1179] Alkyl groups, substituted or unsubstituted, having 1 to 6 carbon atoms.

[1180] R 162 R 164 R 165 and R 167 It is a hydrogen atom.

[1181] In one embodiment of this invention, the first sensitizing material is any one of the compounds represented by the general formulas (101), (106), (107), (110), (111), and (116) to (119). In the general formulas (101), (106), (107), (110), (111), and (116) to (119), D1 is independently a group represented by general formula (1-1), a group represented by general formula (1-2), or a group represented by general formula (1-4), and D2 is independently any one of the groups represented by general formulas (2-5) to (2-14).

[1182] In addition, multiple D1s may be the same as or different from each other, and multiple D2s may be the same as or different from each other.

[1183] In one embodiment of this invention, the first sensitizing material is a compound represented by the general formula (11).

[1184] In one embodiment of this invention, the first sensitizing material is a compound represented by the general formula (12).

[1185] In one embodiment of this invention, the first sensitizing material is a compound represented by the general formula (13).

[1186] In the general formulas (1-1) to (1-6) and (2-1) to (2-4),

[1187] R is preferred as a substituent 101~R 150 R 151 R 152 R 161 ~R 168 R 171 ~R 200 R 171 ~R 180 and R 61 ~R 70 Each independently

[1188] Halogen atoms,

[1189] Unsubstituted aryl groups with 6–14 cyclic carbons

[1190] Unsubstituted heterocyclic groups with 5 to 14 cyclic atoms

[1191] Unsubstituted alkyl groups having 1 to 6 carbon atoms

[1192] Unsubstituted alkyl halogens with 1 to 6 carbon atoms

[1193] Unsubstituted alkylsilyl groups with 3 to 6 carbon atoms

[1194] Unsubstituted alkoxy groups with 1 to 6 carbon atoms,

[1195] Unsubstituted aryloxy groups with 6–14 cyclic carbon atoms,

[1196] Unsubstituted alkylamino groups with 2 to 12 carbon atoms,

[1197] Unsubstituted alkylthio groups with 1 to 6 carbon atoms, or

[1198] Unsubstituted arylthio groups with 6 to 14 cyclic carbons.

[1199] In the general formulas (1-1) to (1-6) and (2-1) to (2-4),

[1200] R is preferred as a substituent 101 ~R 150 R 151 R 152 R 161 ~R 168 R 171 ~R 200 and R 61 ~R 70 Each independently

[1201] Unsubstituted aryl groups with 6 to 14 carbon atoms, or

[1202] Unsubstituted alkyl groups having 1 to 6 carbon atoms.

[1203] In the general formulas (1-1) to (1-6),

[1204] R is also preferred 101 ~R 150 and R 61 ~R 70 It is a hydrogen atom.

[1205] R 151 and R 152 It is an unsubstituted aryl group with 6 to 14 carbon atoms or an unsubstituted alkyl group with 1 to 6 carbon atoms.

[1206] In the general formulas (2-1) to (2-4),

[1207] R is also preferred 161 ~R 168 and R 171 ~R 200 It is a hydrogen atom.

[1208] In one embodiment of this invention, the first sensitizing material is a compound represented by the following general formula (103A).

[1209] [Chemistry 72]

[1210]

[1211] In the general formula (103A), D 10 For groups represented by the following general formula (1-4A), D 20 The group is represented by the general formula (2-1). The plurality of D groups in the general formula (103A) 20 They are groups that are the same as each other.

[1212] "Multiple D" 20 "Groups that are identical to each other" means that all variables in general formula (2-1) represented by the same symbol are identical to each other. "Variables in general formula (2-1)" refers to R... 161 ~R 168 Specifically, in general formula (103A), D represents... 20 In the “group represented by general formula (2-1)”, R 161 They are the same, R 162 They are the same, R 163 They are the same, R 164 They are the same, R 165 They are the same, R 166 They are the same, R 167 They are the same, R 168 They are identical to each other. That is, the three Ds in the general formula (103A) are the same. 20 These are groups that are identical to each other, including substituents.

[1213] [Chemistry 73]

[1214]

[1215] In the general formula (1-4A), X 40 R is an oxygen atom or a sulfur atom. 131 ~R 140 R in the general formulas (1-4) respectively 131 ~R 140 Synonyms.

[1216] * indicates the position where it is bonded to the benzene ring in the general formula (103A).

[1217] In the general formula (1-4A), X is preferred. 40 It is a sulfur atom.

[1218] In the general formula (1-4A), X is also preferred. 40 It is an oxygen atom.

[1219] In the compound represented by the general formula (103A), the group represented by the general formula (2-1) is preferably any one of the groups represented by the general formulas (2-5) and (2-9) to (2-17).

[1220] In the general formulas (2-5) and (2-9) to (2-17), * independently represents the position bonded to the benzene ring in the general formula (103A), and D represents deuterium.

[1221] In the general formula (2-1), R is preferred. 161 ~R 168 Each of the following is independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 14 carbon atoms in a cyclic structure, or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, more preferably a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

[1222] In the general formula (2-1), R is also preferred. 161 R 163 R 166 and R 168 At least one of them has a substituent, which is independently a substituted or unsubstituted aryl group having 6 to 14 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, R 162 R 164 R 165 and R 167 It is a hydrogen atom.

[1223] In the general formula (2-1), in R 161 ~R 168When any one or more of the atoms are hydrogen atoms, it is preferable that all of the hydrogen atoms are protium, or that any one or more of the hydrogen atoms are deuterium, or that all of the hydrogen atoms are deuterium.

[1224] In the general formulas (1-4A) and (2-1), R is preferably used as a substituent. 131 ~R 140 and R 161 ~R 168 Each of the following is independently a halogen atom, an unsubstituted aryl group having 6 to 14 cyclic carbon atoms, an unsubstituted heterocyclic group having 5 to 14 cyclic carbon atoms, an unsubstituted alkyl group having 1 to 6 cyclic carbon atoms, an unsubstituted haloalkyl group having 1 to 6 cyclic carbon atoms, an unsubstituted alkylsilyl group having 3 to 6 cyclic carbon atoms, an unsubstituted alkoxy group having 1 to 6 cyclic carbon atoms, an unsubstituted aryloxy group having 6 to 14 cyclic carbon atoms, an unsubstituted alkylamino group having 2 to 12 cyclic carbon atoms, an unsubstituted alkylthio group having 1 to 6 cyclic carbon atoms, or an unsubstituted arylthio group having 6 to 14 cyclic carbon atoms.

[1225] In the general formulas (1-4A) and (2-1), R is preferred. 131 ~R 140 and R 161 ~R 168 Each of the following is independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 14 cyclic carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 14 cyclic carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 6 cyclic carbon atoms; more preferably, a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 14 cyclic carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 6 cyclic carbon atoms; and even more preferably, a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 6 cyclic carbon atoms.

[1226] In the general formulas (1-4A) and (2-1), R is more preferably a substituent. 131 ~R 140 and R 161 ~R 168 Each is independently an unsubstituted aryl group having 6 to 14 carbon atoms in a cyclic ring, or an unsubstituted alkyl group having 1 to 6 carbon atoms.

[1227] In the general formulas (1-4A) and (2-1), R is also preferred. 137 As a substituent, R as a substituent 137 R is an aryl group with 6 to 14 carbon atoms, either substituted or unsubstituted, or an alkyl group with 1 to 6 carbon atoms, either substituted or unsubstituted. 131 ~R 136 and R 138 ~R 140 It is a hydrogen atom.

[1228] In the general formulas (1-4A) and (2-1), R is also preferred.131 ~R 140 and R 161 ~R 168 It is a hydrogen atom.

[1229] As a specific example of the first sensitizing material (a compound represented by any one of the general formulas (11) to (13)) in this embodiment, the following compounds may be cited as examples. However, the first sensitizing material is not limited to these specific examples of compounds. Me represents methyl.

[1230] [Chemistry 74]

[1231]

[1232] [Chemistry 75]

[1233]

[1234] [Chemistry 76]

[1235]

[1236] [Chemistry 77]

[1237]

[1238] [Chemistry 78]

[1239]

[1240] [Chemistry 79]

[1241]

[1242] [Chemistry 80]

[1243]

[1244] [Chemistry 81]

[1245]

[1246] [Chemistry 82]

[1247]

[1248] [Chemistry 83]

[1249]

[1250] [Chemistry 84]

[1251]

[1252] [Chemistry 85]

[1253]

[1254] [Chemistry 86]

[1255]

[1256] [Chemistry 87]

[1257]

[1258] [Chemistry 88]

[1259]

[1260] [Chemistry 89]

[1261]

[1262] [Chemistry 90]

[1263]

[1264] [Chemistry 91]

[1265]

[1266] [Chemistry 92]

[1267]

[1268] [Chemistry 93]

[1269]

[1270] [Chemistry 94]

[1271]

[1272] [Chem. 95]

[1273]

[1274] [Chemistry 96]

[1275]

[1276] [Chemistry 97]

[1277]

[1278] [Chem. 98]

[1279]

[1280] [Chemistry 99]

[1281]

[1282] [Chemistry 100]

[1283]

[1284] [Chemistry 101]

[1285]

[1286] [Chemistry 102]

[1287]

[1288] [Chemistry 103]

[1289]

[1290] [Chemistry 104]

[1291]

[1292] [Chemistry 105]

[1293]

[1294] [Chemistry 106]

[1295]

[1296] [Chemistry 107]

[1297]

[1298] [Chemistry 108]

[1299]

[1300] [Chemistry 109]

[1301]

[1302] [Chemical 110]

[1303]

[1304] [Chemistry 111]

[1305]

[1306] [Chemistry 112]

[1307]

[1308] [Chemistry 113]

[1309]

[1310] [Chemistry 114]

[1311]

[1312] [Chemistry 115]

[1313]

[1314] [Chemistry 116]

[1315]

[1316] [Chemistry 117]

[1317]

[1318] [Chemistry 118]

[1319]

[1320] [Chemistry 119]

[1321]

[1322] [Chemistry 120]

[1323]

[1324] [Chemistry 121]

[1325]

[1326] [Chemistry 122]

[1327]

[1328] [Chemistry 123]

[1329]

[1330] [Chemistry 124]

[1331]

[1332] [Chemistry 125]

[1333]

[1334] [Chemistry 126]

[1335]

[1336] [Chemistry 127]

[1337]

[1338] [Chemistry 128]

[1339]

[1340] [Chemistry 129]

[1341]

[1342] [Chemistry 130]

[1343]

[1344] [Chemistry 131]

[1345]

[1346] [Chemistry 132]

[1347]

[1348] [Chemistry 133]

[1349]

[1350] [Chemistry 134]

[1351]

[1352] [Chemistry 135]

[1353]

[1354] In one embodiment of this invention, the first sensitizing material is a compound represented by the following general formula (1000).

[1355] [Chemistry 136]

[1356]

[1357] (In general formula (1000),

[1358] Y1 and Y2 are either hydrogen atoms or cyano groups, respectively.

[1359] R1 and R2 are independently...

[1360] hydrogen atom,

[1361] cyano,

[1362] substituted or unsubstituted aryl groups with 6 to 40 carbon atoms

[1363] Substituted or unsubstituted heteroaryl groups with 5 to 40 cyclic atoms, or

[1364] Groups represented by -N(Rz1)(Rz2),

[1365] In this case, R1 and R2 are not both hydrogen atoms.

[1366] The group consisting of Rz1 and Rz2

[1367] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[1368] They bond to each other to form substituted or unsubstituted fused rings, or

[1369] They do not bond with each other.

[1370] Group consisting of L1 and Rz1

[1371] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[1372] They bond to each other to form substituted or unsubstituted fused rings, or

[1373] They do not bond with each other.

[1374] The group consisting of L1 and Rz2

[1375] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[1376] They bond to each other to form substituted or unsubstituted fused rings, or

[1377] They do not bond with each other.

[1378] The group consisting of L2 and Rz1

[1379] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[1380] They bond to each other to form substituted or unsubstituted fused rings, or

[1381] They do not bond with each other.

[1382] Group consisting of L2 and Rz2

[1383] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[1384] They bond to each other to form substituted or unsubstituted fused rings, or

[1385] They do not bond with each other.

[1386] L1 and L2, which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted fused ring, are respectively independently...

[1387] single bond,

[1388] Substituted or unsubstituted ynylene groups with 2 to 18 carbon atoms

[1389] Substituted or unsubstituted arylene groups with 6 to 18 carbon atoms

[1390] Substituted or unsubstituted heteroaryl groups with 5 to 18 cyclic atoms, or

[1391] These groups are groups formed by the bonding of two of their constituent groups.

[1392] Rz1 and Rz2, which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted fused ring, are independently...

[1393] (Aryl groups, substituted or unsubstituted, with 6 to 40 carbon atoms in the cyclic group.)

[1394] One embodiment of the compound represented by the general formula (1000) is a compound represented by the following general formula (1000A) or (1000B).

[1395] [Chemistry 137]

[1396]

[1397] (In the general formulas (1000A) and (1000B), R2 is synonymous with R2 in the general formula (1000).)

[1398] In one embodiment of this invention, the first sensitizing material is a compound represented by the following general formula (1001).

[1399] [Chemistry 138]

[1400]

[1401] (In general formula (1001),

[1402] Y1 and Y2 are either hydrogen atoms or cyano groups, respectively.

[1403] X1 and X2 are independently CH or nitrogen atoms, respectively.

[1404] L1, L2, R1, and R2 are each independently synonymous with L1, L2, R1, and R2 in the general formula (1000).

[1405] One embodiment of the compound represented by the general formula (1001) is a compound represented by the following general formula (1001A) or (1001B).

[1406] [Chemistry 139]

[1407]

[1408] (In the general formulas (1001A) and (1001B), R2 is synonymous with R2 in the general formula (1001).)

[1409] In one embodiment of this invention, the first sensitizing material is a compound represented by the following general formula (1002).

[1410] [Chemistry 140]

[1411]

[1412] (In the general formula (1002),

[1413] L1 and L2 are independently

[1414] single bond,

[1415] Substituted or unsubstituted phenylene

[1416] Substituted or unsubstituted biphenylene, or

[1417] A divalent group derived from substituted or unsubstituted trans-stilbene.

[1418] X1 and X2 are independently

[1419] hydrogen atom,

[1420] substituted or unsubstituted aryl groups with 6 to 40 carbon atoms

[1421] Substituted or unsubstituted heteroaryl groups with 5 to 40 cyclic atoms, or

[1422] Groups represented by -N(Rz1)(Rz2),

[1423] The group consisting of Rz1 and Rz2

[1424] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[1425] They bond to each other to form substituted or unsubstituted fused rings, or

[1426] They do not bond with each other.

[1427] Rz1 and Rz2, which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted fused ring, are independently...

[1428] Substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, or

[1429] Substituted or unsubstituted heteroaryl groups with 5 to 40 carbon atoms in the ring.

[1430] Y1 and Y2 are each independently a group represented by any one of the following general formulas (W-1) to (W-21).

[1431] [Chemistry 141]

[1432]

[1433] [Chemistry 142]

[1434]

[1435] (In the general formulas (W-1) to (W-21), * indicates the bonding position.)

[1436] One embodiment of the compound represented by the general formula (1002) is a compound represented by the following general formula (1002A).

[1437] [Chemistry 143]

[1438]

[1439] (In the general formula (1002A), X1 and X2 are independently synonymous with X1 and X2 in the general formula (1002).)

[1440] In one embodiment of this invention, the first sensitizing material is a compound represented by the following general formula (1003).

[1441] [Chemistry 144]

[1442]

[1443] (In the general formula (1003),

[1444] X3 and X4 are independently...

[1445] hydrogen atom,

[1446] substituted or unsubstituted aryl groups with 6 to 40 carbon atoms

[1447] Substituted or unsubstituted heteroaryl groups with 5 to 40 cyclic atoms, or

[1448] Groups represented by -N(Rz1)(Rz2),

[1449] The group consisting of Rz1 and Rz2

[1450] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[1451] They bond to each other to form substituted or unsubstituted fused rings, or

[1452] They do not bond with each other.

[1453] Rz1 and Rz2, which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted fused ring, are independently...

[1454] Substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, or

[1455] (Substituted or unsubstituted heteroaryl groups with 5 to 40 carbon atoms in the cyclic group.)

[1456] In one embodiment of this invention, the first sensitizing material is a compound represented by any one of the following general formulas (1004A) to (1004D).

[1457] [Chemistry 145]

[1458]

[1459] (In the general formulas (1004A) to (1004D),

[1460] X A for

[1461] substituted or unsubstituted aryl groups with 6 to 50 carbon atoms

[1462] Substituted or unsubstituted heteroaryl groups with 5 to 30 cyclic atoms

[1463] Groups represented by -N(Rz1)(Rz2),

[1464] Y A It can be a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 carbon atoms, or a group represented by -N(Rz1)(Rz2).

[1465] R 1A ~R 2A and R 5A ~R 8AEach of the following groups is independently a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkoxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 carbon atoms, or a group represented by -N(Rz1)(Rz2).

[1466] The group consisting of Rz1 and Rz2

[1467] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[1468] They bond to each other to form substituted or unsubstituted fused rings, or

[1469] They do not bond with each other.

[1470] Rz1 and Rz2, which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted fused ring, are independently...

[1471] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1472] (Substituted or unsubstituted heteroaryl groups with 5 to 50 carbon atoms in the cyclic group.)

[1473] (In the case where Rz1 and Rz2 in -N(Rz1)(Rz2) form the substituted or unsubstituted monocyclic ring or the substituted or unsubstituted fused ring, Rz1 and Rz2 can form a monocyclic or fused ring by bonding with each other via single bonds, by bonding with each other via substituted or unsubstituted methylene groups, or by bonding with each other via oxygen or sulfur atoms.)

[1474] One embodiment of the compound represented by the general formula (1004B) is a compound represented by the following general formula (1004B-1).

[1475] [Chemistry 146]

[1476]

[1477] (In the general formula (1004B-1), X A and Y A Independently related to X in the general formula (1004B) A and Y A Synonyms.

[1478] In one embodiment of this invention, the first sensitizing material is a compound represented by any one of the following general formulas (1005A) to (1005D).

[1479] [Chemistry 147]

[1480]

[1481] (In the general formulas (1005A) to (1005D), X A and Y A Each independently relates to X in the general formulas (1004A) to (1004D). A and Y A Synonyms, R 1A ~R 6A Each independently relates to R in the general formulas (1004A) to (1004D). 1A ~R 2A and R 5A ~R 8A Synonyms

[1482] By R 7B and R 8B The group

[1483] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[1484] They bond to each other to form substituted or unsubstituted fused rings, or

[1485] They do not bond with each other.

[1486] R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 7B and R 8B Each independently relates to R in the general formulas (1004A) to (1004D). 1A ~R 2A and R 5A ~R 8A Synonyms.

[1487] One embodiment of the compound represented by the general formula (1005B) is a compound represented by the following general formulas (1005B-1), (1005B-2), (1005B-3) or (1005B-4).

[1488] [Chemistry 148]

[1489]

[1490] (In the general formulas (1005B-1) and (1005B-2), X A and Y AIndependently related to X in the general formula (1005B) A and Y A Synonyms, R 1005 (This refers to aryl groups with 6 to 50 cyclic carbons, either substituted or unsubstituted, or heteroaryl groups with 5 to 50 cyclic carbons, either substituted or unsubstituted.)

[1491] [Chemistry 149]

[1492]

[1493] (In the general formulas (1005B-3) and (1005B-4), X A and Y A Independently related to X in the general formula (1005B) A and Y A Synonyms.

[1494] In one embodiment of this invention, the first sensitizing material is a compound represented by the following general formula (1006).

[1495] [Chemistry 150]

[1496]

[1497] (In general formula (1006), Ar) 104 and Ar 105 Each independently

[1498] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1499] Heteroaryl groups with 5 to 50 cyclic atoms, whether substituted or unsubstituted.

[1500] Among them, Ar 104 and Ar 105 At least one of them is an aryl group substituted with N,N-diarylamino.

[1501] In the general formula (1006), the aryl group substituted by N,N-diarylamino can be Ar. 104 and Ar 105 One of them, or Ar 104 and Ar 105 Both, but preferably Ar 104 and Ar 105 Both Ar1 and Ar2 are aryl groups substituted with N,N-diarylamino groups. These N,N-diarylamino groups may be the same or different from each other, but are preferably the same.

[1502] In the general formula (1006), one scheme for the aryl group substituted with N,N-diarylamino is a group represented by the following general formula (1006A).

[1503] [Chemistry 151]

[1504]

[1505] (In general formula (1006A),

[1506] Ar 101 for

[1507] Substituted or unsubstituted arylene groups with 6 to 18 carbon atoms, or

[1508] Substituted or unsubstituted heteroaryl groups with 5–18 cyclic atoms.

[1509] Ar 102 and Ar 103 Each independently

[1510] Aryl groups, substituted or unsubstituted, with 6 to 18 carbon atoms in the cyclic group.

[1511] Among them, Ar 102 and Ar 103 The groups formed can be linked by single bonds or by linking groups A.

[1512] * indicates the site where the pyrazine ring is bonded in general formula (1006).

[1513] In general formula (1006A), the linking group A can be substituted or unsubstituted methylene, substituted or unsubstituted ethylene, substituted or unsubstituted vinylene, substituted or unsubstituted imino, oxygen atom, or sulfur atom. Among them, when the ethylene and vinylene are substituted by multiple substituents, the two adjacent substituents can bond to each other to form a cyclic structure.

[1514] In one embodiment of this invention, the first sensitizing material is a compound represented by the following general formula (1007A) or (1007B).

[1515] [Chemistry 152]

[1516]

[1517] (In the general formulas (1007A) and (1007B),

[1518] R 101 ~R 104 Each independently

[1519] hydrogen atom,

[1520] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1521] Substituted or unsubstituted alkoxy groups having 1 to 5 carbon atoms, or

[1522] Substituted or unsubstituted phenyl groups

[1523] X 101 Y 101 X 201 and Y 201 Each independently

[1524] hydrogen atom,

[1525] Substituted or unsubstituted alkyl groups having 1 to 5 carbon atoms

[1526] Substituted or unsubstituted aromatic amino groups, or

[1527] Substituted or unsubstituted aromatic phosphoxy groups.

[1528] In the general formulas (1007A) and (1007B), aromatic amino groups include, for example, alkylamino, arylamino, dialkylamino, and diarylamino.

[1529] One embodiment of the compound represented by the general formula (1007A) is the following general formula (1007A-1), and one embodiment of the compound represented by the general formula (1007B) is the following general formula (1007B-1).

[1530] [Chemistry 153]

[1531]

[1532] (In the general formula (1007A-1), X 101 X in the general formula (1007A) 101 Synonyms.

[1533] (In the general formula (1007B-1), R) 103 R 104 and X 201 R in the general formula (1007B) 103 R 104 and X 201 Synonyms.

[1534] In one embodiment of this invention, the first sensitizing material is a compound represented by the following general formula (1008) or (1008A).

[1535] [Chemistry 154]

[1536]

[1537] (in the general formulas (1008) and (1008A),

[1538] X9 represents either a sulfur atom or a selenium atom.

[1539] By R 82 and R 83 The group

[1540] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[1541] They bond to each other to form substituted or unsubstituted fused rings, or

[1542] They do not bond with each other.

[1543] R 81 and R 84 R, and R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 82 and R 83 The following groups are independently composed of hydrogen atoms, hydroxyl groups, halogen atoms, cyano groups, substituted or unsubstituted alkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted alkoxy groups with 1 to 20 carbon atoms, substituted or unsubstituted alkylthio groups with 1 to 20 carbon atoms, substituted or unsubstituted alkyl-substituted amino groups with 1 to 20 carbon atoms, substituted or unsubstituted aryl-substituted amino groups with 6 to 40 carbon atoms, substituted or unsubstituted acyl groups with 2 to 20 carbon atoms, substituted or unsubstituted cyclic aryl groups with 6 to 40 carbon atoms, substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms, substituted or unsubstituted alkenyl groups with 2 to 10 carbon atoms, and substituted or unsubstituted carbon atoms. The following groups are included: alkynyl (2-10 carbon groups), substituted or unsubstituted alkoxycarbonyl (2-10 carbon groups), substituted or unsubstituted alkylsulfonyl (1-10 carbon groups), substituted or unsubstituted haloalkyl (1-10 carbon groups), substituted or unsubstituted amide (2-10 carbon groups), substituted or unsubstituted alkylamide (3-20 carbon groups), substituted or unsubstituted trialkylsilyl (4-20 carbon groups), substituted or unsubstituted trialkylsilylalkyl (5-20 carbon groups), substituted or unsubstituted trialkylsilylalkynyl (5-20 carbon groups), or nitro.

[1544] Among them, R 81 ~R 84 At least two of them are independently groups represented by the general formula (1008B).

[1545] (In the general formula (1008B), L8 is)

[1546] Substituted or unsubstituted arylene groups with 6 to 40 carbon atoms, or

[1547] Substituted or unsubstituted heteroaryl groups with 5 to 40 cyclic atoms

[1548] n1 is either 0 or 1.

[1549] X1 to X8 are each independently a nitrogen atom or a CR atom. 1008 Among them, at least one of X1 to X8 is CR. 1008 ,

[1550] By adjacent R 1008 One or more groups constituted

[1551] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[1552] They bond to each other to form substituted or unsubstituted fused rings, or

[1553] They do not bond with each other.

[1554] R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 1008 Independently related to R in the general formulas (1008) and (1008A) respectively. 81 and R 84 Synonyms

[1555] Multiple R 1008 (They may be the same as or different from each other.)

[1556] One embodiment of the compounds represented by the general formulas (1008) and (1008A) is a compound represented by any one of the following general formulas (1008-1) to (1008-7).

[1557] [Chemistry 155]

[1558]

[1559] (In the general formulas (1008-1) to (1008-7), X 10 R is a sulfur atom or a selenium atom. 85 ~R 87 Independently related to R in the general formulas (1008) and (1008A) respectively. 81 Synonyms, X9, R 81 and R 84 Independently related to X9 and R in the general formulas (1008) and (1008A), respectively. 81 and R 84 Synonyms.

[1560] In one embodiment of this invention, the first sensitizing material is a compound represented by any one of the following general formulas (1009A) to (1009C).

[1561] [Chemistry 156]

[1562]

[1563] [Chemistry 157]

[1564]

[1565] (In the general formulas (1009A) to (1009C),

[1566] X9 represents either a sulfur atom or a selenium atom.

[1567] X is

[1568] Substituted or unsubstituted arylene groups with 6 to 20 carbon atoms in the cyclic group,

[1569] Substituted or unsubstituted heteroaryl groups with 3 to 20 cyclic atoms

[1570] From substituted or unsubstituted arylene groups with 6 to 20 carbon atoms, and

[1571] A group formed by the bonding of two or three groups selected from substituted or unsubstituted heteroaryl groups having a cyclic number of 3 to 20 atoms.

[1572] Y is

[1573] substituted or unsubstituted aryl groups with 6 to 20 carbon atoms in the cyclic group,

[1574] Substituted or unsubstituted heteroaryl groups with 3 to 20 cyclic atoms, or

[1575] Groups represented by -N(Rz1)(Rz2),

[1576] Rz1 and Rz2 are independently...

[1577] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1578] Substituted or unsubstituted heteroaryl groups with 5 to 50 carbon atoms in the cyclic structure.

[1579] R1 and R2 are independently...

[1580] hydrogen atom,

[1581] Substituted or unsubstituted carbazolyl, or

[1582] Substituted or unsubstituted diphenylamine group,

[1583] (Among them, at least one of R1 and R2 is a hydrogen atom.)

[1584] In one embodiment of this invention, the first sensitizing material is a compound represented by the following general formula (1010).

[1585] [Chemistry 158]

[1586]

[1587] (In the general formula (1010), R) 1 ~R 7 Each can independently represent a hydrogen atom or a substituent, R 1 and R 2 group, R 2 and R 3 group, R 3 and R 4 group, R 4 and R 5 group, R 5 and R 6 The group, and R 6 and R 7 Any one or more groups within a set can bond together to form a ring.

[1588] R 7 This refers to a group represented by the following general formula (1010A) or general formula (1010B).

[1589] [Chemistry 159]

[1590]

[1591] (in the general formula (1010A)),

[1592] Ar 11 These are groups derived from substituted or unsubstituted aryl groups with 6 to 40 cyclic carbon atoms.

[1593] R 11 Indicates substituents other than aryl, n 11 Indicates 1 to Ar 11 An integer up to the number of positions that can be replaced.

[1594] n 11 When the value is 2 or higher, multiple R 11 The same or different, wherein at least one R 11 (It is an electron-donating group.)

[1595] (In the general formula (1010B), R) 21 ~R 25 Each can be represented independently by a hydrogen atom or a substituent, where p is an integer from 0 to 2.

[1596] (In the general formulas (1010), (1010A) and (1010B), R as a substituent) 1 ~R 6 R 11 and R 21 ~R 25 These groups can be independently halogen atoms, alkyl, alkenyl, alkynyl, aryl, heteroaryl, halogen atoms, hydroxyl, nitro, carboxyl, cyano, alkoxy, aryloxy, acyl, acyloxy, carbamoyloxy (alkoxycarbonyloxy, etc.), primary amino, alkylamino, arylamino, dialkylamino, diarylamino, alkylarylamino, acylamino, aminocarbonylamino, alkoxycarbonylamino, aryloxycarbonylamino, aminosulfonylamino, alkylsulfonylamino, arylsulfonylamino, alkylthio, arylthio, sulfonyl, aminosulfonyl, alkylsulfinyl, arylsulfinyl, alkylsulfonyl, arylsulfonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, imino, alkoxysulfonyl, aryloxysulfonyl, trialkylsilyl or trialkylsilyloxy. These groups can be further substituted.

[1597] In one embodiment of this invention, the first sensitizing material is a compound represented by the following general formula (1011A) or (1011B).

[1598] [Chemistry 160]

[1599]

[1600] In the general formulas (1011A) and (1011B), M is independently selected from the group consisting of C(R1)2, NR1, O atom, S atom, SO2, P(=O)R1, Si(R1)2, Ge(R1)2 and groups represented by the following general formulas (M-1) to (M-5),

[1601] R1 can be independently a hydrogen atom, fluorine atom, chlorine atom, bromine atom, iodine atom, cyano group, -NO2, -N(R2)2, -OR2, -SR2, -C(=O)R2, -P(=O)R2, -Si(R2)3, an alkyl group with 1 to 20 substituted or unsubstituted carbon atoms, an alkenyl group with 2 to 20 substituted or unsubstituted carbon atoms, an aryl group with 6 to 40 substituted or unsubstituted cyclic carbon atoms, or a heteroaryl group with 3 to 40 substituted or unsubstituted cyclic carbon atoms.

[1602] R2 can be independently a hydrogen atom, a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic group having 3 to 30 heteroaryl groups.

[1603] Multiple M's may be the same or different from each other.

[1604] In the case of multiple R1s, the multiple R1s may be the same or different from each other.

[1605] In the case of multiple R2s, these R2s may be the same as or different from each other.

[1606]

[1607] (In the general formulas (M-1) to (M-5), X is a substituted or unsubstituted alkyl group with 1 to 8 carbon atoms or a single bond; Y is C(R1)2, NR1, carbonyl, O atom, S atom, SO2, P(=O)R1, Si(R1)2, Ge(R1)2 or a single bond; Z is CR1 or a nitrogen atom. The R1 in Y and the R1 in Z are independently synonymous with the R1 in the general formula (1011A). In the case of multiple R1s, the multiple R1s may be the same or different from each other, and the multiple Zs may be the same or different. * indicates the bonding position.)

[1608] In one embodiment of this invention, the first sensitizing material is a compound represented by the following general formula (1012A) or (1012B).

[1609] [Chemistry 161]

[1610]

[1611] (In the general formulas (1012A) and (1012B),

[1612] D1 and D4 can be the same electron-donating group or hydrogen atom, or D1 and D4 can be different electron-donating groups.

[1613] D2 and D3 can be the same electron-donating group or hydrogen atom, or D2 and D3 can be different electron-donating groups.

[1614] The electron-donating group is selected from one of the following: substituted or unsubstituted carbazole, substituted or unsubstituted acridine, substituted or unsubstituted phenoxazine, substituted or unsubstituted phenazine, substituted or unsubstituted phenazine, and substituted or unsubstituted phenothiazine. In the case of substitution or unsubstitution, the substituent is one or more of methyl, ethyl, isopropyl, tert-butyl, phenyl, carbazole, substituted or unsubstituted amino, acridine, phenazine, fluorenyl, dibenzofuranyl, and dibenzothiophene.

[1615] In one embodiment of this invention, the first sensitizing material is a compound represented by the following general formula (1013).

[1616] [Chemistry 162]

[1617]

[1618] (In the general formula (1013), Z) 1 Z 2 and Z 3 Each substituent can be represented independently; the substituent is an atom or group of atoms other than hydrogen.

[1619] In the general formula (1013), Z is preferred. 1 Z 2 and Z 3 The substituents represented are, independently, substituted amino groups (e.g., dialkylamino, diarylamino, alkylarylamino, etc.), substituted or unsubstituted aryl groups with 6 to 50 carbon atoms in the cyclic structure, or substituted or unsubstituted heteroaryl groups with 5 to 50 cyclic atoms. Z is preferred. 1 Z 2 and Z 3 They are the same.

[1620] In one embodiment of this invention, the first sensitizing material is a compound represented by the following general formula (1014).

[1621] [Chemistry 163]

[1622]

[1623] (In the general formula (1014),

[1624] By R 1 ~R 8 One or more groups consisting of two or more adjacent elements.

[1625] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[1626] They bond to each other to form substituted or unsubstituted fused rings, or

[1627] They do not bond with each other.

[1628] R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 1 ~R 8 Each can independently represent a hydrogen atom or a substituent, R 1 ~R 8 At least one of them is a group represented by the following general formula (1014A).

[1629] [Chemistry 164]

[1630]

[1631] (In the general formula (1014A), Ar) 1This indicates a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group. n1 indicates 0 or 1.

[1632] By R 11 ~R 20 One or more groups consisting of two or more adjacent elements.

[1633] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[1634] They bond to each other to form substituted or unsubstituted fused rings, or

[1635] They do not bond with each other.

[1636] R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 11 ~R 20 Each can be represented independently as a hydrogen atom or a substituent.

[1637] In the general formulas (1014) and (1014A), R is preferred. 1 ~R 8 and R 11 ~R 20 It is independently composed of a hydrogen atom, a hydroxyl group, a halogen atom, a cyano group, an alkyl group with 1 to 20 carbon atoms, an alkoxy group with 1 to 20 carbon atoms, an alkylthio group with 1 to 20 carbon atoms, an alkyl-substituted amino group with 1 to 20 carbon atoms, an acyl group with 2 to 20 carbon atoms, an aryl group with 6 to 40 carbon atoms, a heteroaryl group with 3 to 40 carbon atoms, an alkenyl group with 2 to 10 carbon atoms, an alkynyl group with 2 to 10 carbon atoms, an alkoxycarbonyl group with 2 to 10 carbon atoms, an alkylsulfonyl group with 1 to 10 carbon atoms, a haloalkyl group with 1 to 10 carbon atoms, an amide group, an alkylamide group with 2 to 10 carbon atoms, a trialkylsilyl group with 3 to 20 carbon atoms, a trialkylsilylalkyl group with 4 to 20 carbon atoms, a trialkylsilylalkylalkenyl group with 5 to 20 carbon atoms, a trialkylsilylalkylalkynyl group with 5 to 20 carbon atoms, or a nitro group.

[1638] In the general formula (1014A), Ar 1 In cases of "substituted or unsubstituted", the substituents are independently associated with R in the general formulas (1014) and (1014A), respectively. 1 ~R 8 and R 11 ~R 20 (But except for hydrogen atoms) are synonyms.

[1639] In one embodiment of this invention, the first sensitizing material is a compound represented by the following general formula (1015).

[1640] [Chemistry 165]

[1641]

[1642] (In the general formula (1015), X is an oxygen atom or a sulfur atom,

[1643] By R 1 ~R 8 One or more groups consisting of two or more adjacent elements.

[1644] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[1645] They bond to each other to form substituted or unsubstituted fused rings, or

[1646] They do not bond with each other.

[1647] R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 1 ~R 8 Each can be independently represented by a hydrogen atom or a substituent, where R 1 ~R 8 At least one of them is independently a group represented by any one of the following general formulas (1015A) to (1015E).

[1648] [Chemistry 166]

[1649]

[1650] (In the general formulas (1015A) to (1015E), L 20 L 30 L 40 L 50 and L 60 Each of these groups independently represents a single bond or a divalent linker, *bonded to the ring skeleton of general formula (1015).

[1651] By R 21 ~R 28 One or more groups consisting of two or more adjacent elements.

[1652] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[1653] They bond to each other to form substituted or unsubstituted fused rings, or

[1654] They do not bond with each other.

[1655] By R 31 ~R 38 One or more groups consisting of two or more adjacent elements.

[1656] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[1657] They bond to each other to form substituted or unsubstituted fused rings, or

[1658] They do not bond with each other.

[1659] By R 3a and R 3b The group

[1660] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[1661] They bond to each other to form substituted or unsubstituted fused rings, or

[1662] They do not bond with each other.

[1663] By R 41 ~R 48 One or more groups consisting of two or more adjacent elements.

[1664] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[1665] They bond to each other to form substituted or unsubstituted fused rings, or

[1666] They do not bond with each other.

[1667] By R 51 ~R 58 One or more groups consisting of two or more adjacent elements.

[1668] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[1669] They bond to each other to form substituted or unsubstituted fused rings, or

[1670] They do not bond with each other.

[1671] By R 61 ~R 68 One or more groups consisting of two or more adjacent elements.

[1672] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[1673] They bond to each other to form substituted or unsubstituted fused rings, or

[1674] They do not bond with each other.

[1675] R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 21 ~R 28 R 31 ~R 38 R 3a R 3b R41 ~R 48 R 4a R 51 ~R 58 and R 61 ~R 68 Each can be represented independently as a hydrogen atom or a substituent.

[1676] In the general formulas (1015A) to (1015E), L is preferred. 20 L 30 L 40 L 50 and L 60 Each of these groups can be independently a single bond, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted ynyl group having 2 to 10 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 10 carbon atoms, a substituted or unsubstituted thiophene diyl group, or a combination thereof. Examples of thiophene diyl groups include 3,4-thiophene diyl and 2,5-thiophene diyl.

[1677] In the general formulas (1015) and (1015A) to (1015E), R is preferred. 1 ~R 8 R 21 ~R 28 R 31 ~R 38 R 3a R 3b R 41 ~R 48 R 4a R 51 ~R 58 and R 61 ~R 68 It is independently composed of a hydrogen atom, a hydroxyl group, a halogen atom, a cyano group, an alkyl group with 1 to 20 carbon atoms, an alkoxy group with 1 to 20 carbon atoms, an alkylthio group with 1 to 20 carbon atoms, an alkyl-substituted amino group with 1 to 20 carbon atoms, an acyl group with 2 to 20 carbon atoms, an aryl group with 6 to 40 carbon atoms, a heteroaryl group with 3 to 40 carbon atoms, an alkenyl group with 2 to 10 carbon atoms, an alkynyl group with 2 to 10 carbon atoms, an alkoxycarbonyl group with 2 to 10 carbon atoms, an alkylsulfonyl group with 1 to 10 carbon atoms, a haloalkyl group with 1 to 10 carbon atoms, an amide group, an alkylamide group with 2 to 10 carbon atoms, a trialkylsilyl group with 3 to 20 carbon atoms, a trialkylsilylalkyl group with 4 to 20 carbon atoms, a trialkylsilylalkylalkenyl group with 5 to 20 carbon atoms, a trialkylsilylalkylalkynyl group with 5 to 20 carbon atoms, or a nitro group.

[1678] In one embodiment of this invention, the first sensitizing material is a compound represented by the following general formula (1016A) or (1016B).

[1679] [Chemistry 167]

[1680]

[1681] (In the general formula (1016A), R) 16A R 16B and R 16C Each substituent can be represented independently; the substituent is an atom or group of atoms other than hydrogen.

[1682] (In the general formula (1016B), R) 16D R 16E R 16F and R 16G Each can be represented independently as a hydrogen atom or a substituent.

[1683] In the general formula (1016A), R is preferred. 16A R 16B and R 16C The substituents represented are, independently, substituted amino groups (e.g., dialkylamino, diarylamino, alkylarylamino, etc.), substituted or unsubstituted aryl groups with 6 to 50 carbon atoms in the cyclic structure, and substituted or unsubstituted heteroaryl groups with 5 to 50 cyclic atoms.

[1684] In the general formula (1016B), R is preferred. 16D R 16E R 16F and R 16G It is independently composed of a hydrogen atom, a hydroxyl group, a halogen atom, a cyano group, an alkyl group with 1 to 20 carbon atoms, an alkoxy group with 1 to 20 carbon atoms, an alkylthio group with 1 to 20 carbon atoms, an alkyl-substituted amino group with 1 to 20 carbon atoms, an acyl group with 2 to 20 carbon atoms, an aryl group with 6 to 40 carbon atoms, a heteroaryl group with 3 to 40 carbon atoms, an alkenyl group with 2 to 10 carbon atoms, an alkynyl group with 2 to 10 carbon atoms, an alkoxycarbonyl group with 2 to 10 carbon atoms, an alkylsulfonyl group with 1 to 10 carbon atoms, a haloalkyl group with 1 to 10 carbon atoms, an amide group, an alkylamide group with 2 to 10 carbon atoms, a trialkylsilyl group with 3 to 20 carbon atoms, a trialkylsilylalkyl group with 4 to 20 carbon atoms, a trialkylsilylalkylalkenyl group with 5 to 20 carbon atoms, a trialkylsilylalkylalkynyl group with 5 to 20 carbon atoms, or a nitro group.

[1685] In the first sensitizing material of this embodiment, specific examples of compounds represented by any one of the general formulas (1000) to (1003), (1004A) to (1004D), (1005A) to (1005D), (1006), (1007A), (1007B), (1008), (1008A), (1009A) to (1009C), (1010), (1011A), (1011B), (1012A), (1012B), (1013) to (1015), (1016A), and (1016B) can be exemplified by the following compounds. However, the first sensitizing material is not limited to these specific examples of compounds. t-C4H9 represents tert-butyl.

[1686] [Chemistry 168]

[1687]

[1688] [Chemistry 169]

[1689]

[1690] [Chemistry 170]

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[1848] [Chemistry 249]

[1849]

[1850] [Chemistry 250]

[1851]

[1852] [Chemistry 251]

[1853]

[1854] [Chemistry 252]

[1855]

[1856] [Chemistry 253]

[1857]

[1858] [Chemistry 254]

[1859]

[1860] [Chemistry 255]

[1861]

[1862] [Chemistry 256]

[1863]

[1864] [Chemistry 257]

[1865]

[1866] [Chemistry 258]

[1867]

[1868] [Chemistry 259]

[1869]

[1870] [Chemistry 260]

[1871]

[1872] [Chemistry 261]

[1873]

[1874] [Chemistry 262]

[1875]

[1876] [Chemistry 263]

[1877]

[1878] [Chemistry 264]

[1879]

[1880] [Chemistry 265]

[1881]

[1882] [Chemistry 266]

[1883]

[1884] [Chemistry 267]

[1885]

[1886] [Chemistry 268]

[1887]

[1888] [Chemistry 269]

[1889]

[1890] [Chemistry 270]

[1891]

[1892] [Chemistry 271]

[1893]

[1894] [Chemistry 272]

[1895]

[1896] [Chemistry 273]

[1897]

[1898] [Chemistry 274]

[1899]

[1900] [Chemistry 275]

[1901]

[1902] [Chemistry 276]

[1903]

[1904] [Chemistry 277]

[1905]

[1906] [Chemistry 278]

[1907]

[1908] [Chemistry 279]

[1909]

[1910] [Chemistry 280]

[1911]

[1912] [Chemistry 281]

[1913]

[1914] [Chemistry 282]

[1915]

[1916] [Chemistry 283]

[1917]

[1918] [Chemistry 284]

[1919]

[1920] [Chemistry 285]

[1921]

[1922] [Chemistry 286]

[1923]

[1924] [Chemistry 287]

[1925]

[1926] [Chemistry 288]

[1927]

[1928] In one embodiment of this invention, the first sensitizing material is a delayed fluorescence material.

[1929] The delayed fluorescence property is explained.

[1930] Delayed fluorescence

[1931] Delayed fluorescence is explained on pages 261-268 of "Device Properties of Organic Semiconductors" (edited by Chihaya Adachi, published by Kodansha). This literature states that if the energy difference ΔE between the excited singlet and excited triplet states of a fluorescent material can be reduced... 13 In this case, the reverse energy transfer from the excited triplet state to the excited singlet state, which typically has a low migration probability, occurs efficiently, producing thermally activated delayed fluorescence (TADF). Furthermore, based on the data in this literature... Figure 10 .38 illustrates the mechanism of delayed fluorescence.

[1932] The first sensitizing material in this embodiment is preferably a compound exhibiting thermally activated delayed fluorescence (TRF) generated by such a mechanism. In this embodiment, the compound exhibiting TRF functions as the sensitizing material.

[1933] Typically, delayed fluorescence can be confirmed by transition PL (photoluminescence) measurements.

[1934] Furthermore, the behavior of delayed fluorescence can be analyzed based on the decay curve obtained from transition PL measurements. Transition PL measurement refers to the method of irradiating the sample with a pulsed laser to excite it and measuring the decay behavior (transition characteristics) of PL emission after irradiation stops. PL emission in TADF materials consists of two components: the emission component from singlet excitons generated by the initial PL excitation and the emission component from singlet excitons generated via triplet excitons. The lifetime of the singlet excitons generated by the initial PL excitation is on the order of nanoseconds, which is very short. Therefore, the emission from these singlet excitons decays rapidly after pulsed laser irradiation.

[1935] On the other hand, delayed fluorescence originates from the emission of singlet excitons generated via long-lived triplet excitons, and therefore decays slowly. Consequently, there is a significant time difference between the emission of singlet excitons generated from the initial PL excitation and the emission of singlet excitons generated via triplet excitons. Therefore, the emission intensity originating from delayed fluorescence can be determined.

[1936] Figure 5 The diagram shows a schematic of an example apparatus for measuring transient PL. Figure 5 The method for measuring transition PL and an example of analyzing the behavior of delayed fluorescence are explained.

[1937] Figure 5The transition PL measurement device 1000 includes: a pulsed laser unit 1010 for irradiating light of a specified wavelength; a sample chamber 1020 for housing the measurement sample; a beam splitter 1030 for splitting the light emitted from the measurement sample; a streak camera 1040 for imaging a two-dimensional image; and a personal computer 1050 for reading and analyzing the two-dimensional image. Furthermore, the measurement of transition PL is not limited to... Figure 5 The device described.

[1938] The sample housed in the sample chamber 1020 can be obtained by forming a thin film on a quartz substrate by doping the matrix material with a dopant material at a concentration of 12% by mass.

[1939] For the thin film sample housed in the sample chamber 1020, a pulsed laser is irradiated from the pulsed laser unit 1010 to excite the doped material. The emitted light is extracted in a direction 90 degrees relative to the irradiation direction of the excitation light, and the extracted light is split by a beam splitter 1030 to form a two-dimensional image in a streak camera 1040. The result is a two-dimensional image with the vertical axis corresponding to time, the horizontal axis corresponding to wavelength, and the bright spots corresponding to emission intensity. If this two-dimensional image is cut along a predetermined time axis, an emission spectrum with emission intensity as the vertical axis and wavelength as the horizontal axis can be obtained. Furthermore, if this two-dimensional image is cut along a wavelength axis, a decay curve (transition pulse) with the logarithm of emission intensity as the vertical axis and time as the horizontal axis can be obtained.

[1940] For example, using the following reference compound H1 as the matrix material and the following reference compound D1 as the dopant material, thin film sample A was prepared as described above, and transition PL measurements were performed.

[1941] [Chemistry 289]

[1942]

[1943] Here, the decay curves were analyzed using the aforementioned thin film sample A and thin film sample B. Thin film sample B was prepared as described above using the reference compound H2 as the matrix material and the reference compound D1 as the dopant material.

[1944] Figure 6 The attenuation curves obtained from the transition PL measured on thin film sample A and thin film sample B are shown in the figure.

[1945] [Chemistry 290]

[1946]

[1947] As described above, by measuring the transition PL (luminescence intensity), a luminescence decay curve can be obtained with luminescence intensity as the vertical axis and time as the horizontal axis. Based on this luminescence decay curve, the fluorescence intensity ratio of fluorescence emitted from a singlet excited state generated by photoexcitation to delayed fluorescence emitted from a singlet excited state generated via reverse energy transfer from a triplet excited state can be calculated. In materials with delayed fluorescence, the proportion of slowly decaying delayed fluorescence intensity is relatively large compared to the intensity of rapidly decaying fluorescence.

[1948] Specifically, luminescence from materials with delayed fluorescence can be categorized into prompt luminescence and delayed luminescence. Prompt luminescence refers to luminescence that is immediately observed from the excited state after being excited by a pulse of light (light from a pulsed laser) of a wavelength absorbed by the material with delayed fluorescence. Delay luminescence refers to luminescence that is not immediately observed after being excited by the pulse of light but is observed later.

[1949] The amounts of Prompt and Delay luminescence, and their ratio, can be determined using the same method as described in "Nature 492, 234-238, 2012" (Reference 1). Furthermore, the apparatus used to calculate the amounts of Prompt and Delay luminescence is not limited to the apparatus described in Reference 1. Figure 5 The device described in the text.

[1950] In this specification, when the first sensitizing material is a delayed-fluorescence material, a sample prepared by the following method is used in the measurement of delayed fluorescence. For example, the target compound (first sensitizing material) is dissolved in toluene, and a dilute solution with an absorbance of 0.05 or less at the excitation wavelength is prepared to eliminate the effect of self-absorption. Furthermore, to prevent extinction caused by oxygen, the sample solution is frozen and degassed, and then sealed in a covered cell under an argon atmosphere, thereby preparing an oxygen-free sample solution saturated with argon.

[1951] The fluorescence spectra of the above sample solutions were measured using a spectrophotometer FP-8600 (manufactured by Nippon Spectrophotometer Co., Ltd.). Additionally, the fluorescence spectrum of the ethanol solution of 9,10-dibenzane was measured under the same conditions. Using the fluorescence area intensities of the two spectra, the total fluorescence quantum yield was calculated according to equation (1) in Morris et al., J. Phys. Chem., 80(1976)969.

[1952] In this embodiment, the amount of prompt luminescence (instantaneous luminescence) of the target compound (first sensitizing material) is denoted as X. P The amount of delayed emission is denoted as X. D At that time, XD / X P The value is preferably 0.05 or higher.

[1953] The measurements of the amount and ratio of Prompt and Delay luminescence for compounds other than the first sensitizing material in this specification are the same as those for the first sensitizing material.

[1954] ·ΔST

[1955] In this embodiment, the minimum excited singlet energy S1 is compared with the bandgap T at 77 [K]. 77K The difference (S1-T) 77K ) is defined as ΔST.

[1956] • Relationship between triplet energy and band gap at 77 K

[1957] Here, the relationship between the triplet energy and the band gap at 77 [K] is explained. In this embodiment, the band gap at 77 [K] differs from the normally defined triplet energy.

[1958] The triplet energy was measured as follows. First, the compound to be measured was dissolved in a suitable solvent, and the resulting solution was sealed in a quartz glass tube to prepare a sample. For this sample, the phosphorescence spectrum (with the vertical axis representing phosphorescence intensity and the horizontal axis representing wavelength) was measured at a low temperature (77 K). A tangent was drawn to the rising edge of the short wavelength side of the phosphorescence spectrum, and the triplet energy was calculated based on the wavelength value of the intersection of the tangent and the horizontal axis according to a prescribed conversion formula.

[1959] In this embodiment, the compound with thermally activated delayed fluorescence (ΔST) is preferably a compound with a small ΔST. If ΔST is small, intersystem crossing and reverse intersystem crossing are more likely to occur even at low temperatures (77 K), resulting in the coexistence of excited singlet and excited triplet states. As a result, the spectrum measured in the same manner as described above can be considered to contain emission from both the excited singlet and excited triplet states. Although it is difficult to distinguish which state the emission originates from, the triplet energy value is essentially dominant.

[1960] Therefore, in this embodiment, the measurement method is the same as that for the usual triplet energy T, but in order to distinguish it strictly, the measured value is referred to as the bandgap T. 77KThe compound to be measured was dissolved in EPA (diethyl ether: isopentane: ethanol = 5:5:2 (volume ratio)) at a concentration of 10 μmol / L, and the solution was placed in a quartz cell as the measurement sample. For this measurement sample, the phosphorescence spectrum (with the vertical axis representing phosphorescence intensity and the horizontal axis representing wavelength) was measured at a low temperature (77 K). A tangent was drawn to the rising edge of the short wavelength side of the phosphorescence spectrum, and the wavelength value λ at the intersection of this tangent and the horizontal axis was determined. edge [nm], the energy calculated according to the following conversion formula (F1) is taken as the band gap T at 77[K]. 77K .

[1961] Conversion formula (F1): T 77K [eV] = 1239.85 / λ edge

[1962] The tangent to the rising edge of the short-wavelength side of the phosphorescence spectrum is drawn as shown below. Consider this tangent as it moves along the spectral curve from the short-wavelength side of the phosphorescence spectrum to the maximum value on the shortest wavelength side of the spectrum, towards the points on the long-wavelength side. The slope of this tangent increases as the curve rises (i.e., as the value on the vertical axis increases). The tangent drawn at the point where this slope reaches its maximum (i.e., the tangent at the inflection point) is taken as the tangent to the rising edge of the short-wavelength side of the phosphorescence spectrum.

[1963] Furthermore, the maximum point of peak intensity with less than 15% of the maximum peak intensity of the spectrum is not included in the maximum value on the shortest wavelength side mentioned above. The tangent line drawn at the point closest to the maximum value on the shortest wavelength side and where the slope value is the maximum value is taken as the tangent line for the rising edge of the short wavelength side of the phosphorescence spectrum.

[1964] Phosphorescence can be measured using the main body of the Hitachi High Technology Co., Ltd. F-4500 spectrophotometer. However, the measuring device is not limited to this; measurements can be performed by combining a cooling device, a cryogenic container, an excitation source, and a light-receiving device.

[1965] • Lowest excited singlet energy S1

[1966] The following methods can be cited as examples of methods for measuring the lowest excited singlet energy S1 using a solution (sometimes called the solution method).

[1967] A 10 μmol / L toluene solution of the compound to be measured was prepared and placed in a quartz cell. The absorption spectrum of the sample was measured at room temperature (300 K) (vertical axis: absorption intensity, horizontal axis: wavelength). A tangent was drawn to the falling edge of the longer wavelength side of the absorption spectrum. The wavelength value λedge [nm] at the intersection of the tangent and the horizontal axis was substituted into the following conversion formula (F2) to calculate the lowest excited singlet energy.

[1968] Conversion formula (F2): S1[eV]=1239.85 / λedge

[1969] As an absorption spectroscopy measuring device, an example of such a device is the Hitachi spectrophotometer (device name: U3310), but it is not limited to this.

[1970] The tangent to the falling edge of the absorption spectrum on the longer wavelength side is plotted as shown below. Consider this tangent at various points on the spectral curve as the maximum value on the longest wavelength side of the absorption spectrum is moved along the longer wavelength direction. This tangent repeatedly shows a decreasing and then increasing slope as the curve descends (i.e., as the vertical axis value decreases). The tangent drawn at the point where the slope is minimized on the longest wavelength side (excluding cases where absorbance is below 0.1) is taken as the tangent to the falling edge of the longer wavelength side of the absorption spectrum.

[1971] In addition, the maximum absorbance values ​​below 0.2 are not included in the maximum values ​​on the longest wavelength side mentioned above.

[1972] In one embodiment of this invention, when the luminescent region is made to emit light, the delayed fluorescence ratio is greater than 37.5%.

[1973] If the delayed fluorescence ratio is greater than 37.5%, it exceeds the theoretical upper limit of the delayed fluorescence ratio (TTF ratio) when delayed fluorescence is generated only through the TTF mechanism, thus enabling the realization of organic EL devices with higher internal quantum efficiency.

[1974] The delayed fluorescence ratio is equivalent to the ratio of the luminescence intensity originating from delayed fluorescence to the total luminescence intensity. The delayed fluorescence ratio is derived using the following calculation method.

[1975] Calculation method of delayed fluorescence ratio

[1976] The delayed fluorescence ratio can be measured using the transition EL method. The transition EL method refers to the method of measuring the decay behavior (transition characteristics) of EL emission after the removal of the pulse voltage applied to the device. EL emission intensity can be divided into two parts: the emission component from singlet excitons generated in the initial recombination, and the emission component from singlet excitons generated via triplet excitons. The singlet excitons generated in the initial recombination have a very short lifetime, on the order of nanoseconds, and therefore decay rapidly after the pulse voltage is removed.

[1977] On the other hand, delayed fluorescence is the emission of singlet excitons generated via long-lived triplet excitons, and therefore decays slowly. Thus, there is a significant temporal difference between the emission of singlet excitons generated in the initial recombination and the emission of singlet excitons generated via triplet excitons, allowing the determination of the emission intensity originating from delayed fluorescence. Specifically, this can be determined using the following method.

[1978] The transition EL waveform is measured in the following manner (refer to...) Figure 7 The pulsed voltage waveform output from the voltage pulse generator (PG) 11 is applied to the organic EL element (EL) 12. The applied voltage waveform is captured and input to the oscilloscope (OSC) 13P. When a pulsed voltage is applied to the organic EL element 12P, the organic EL element 12P generates pulsed light emission. This light emission is captured and input to the oscilloscope (OSC) 13P via the photomultiplier tube (PMT) 14P. The voltage waveform is synchronized with the pulsed light emission and input to the personal computer (PC) 15P.

[1979] By analyzing the transition EL waveform, the luminescence intensity ratio derived from delayed fluorescence (the delayed fluorescence ratio in this specification) is defined as follows. Furthermore, to calculate the luminescence intensity ratio derived from delayed fluorescence, the formula for calculating the TTF ratio described in International Publication No. 2010 / 134352 can be used.

[1980] The delayed fluorescence ratio is calculated using mathematical formula (4).

[1981] [Number 1]

[1982]

[1983] In mathematical formula (4), I represents the luminescence intensity originating from delayed fluorescence, and A is a constant. Therefore, the constant A is obtained by fitting the measured transition EL waveform data using mathematical formula (4). At this time, the luminescence intensity 1 / A at the moment t=0, after removing the pulse voltage, is calculated. 2 Defined as the ratio of luminescence intensity originating from delayed fluorescence.

[1984] Figure 8A The graphs are measurement examples of the transition EL waveforms of the organic EL elements of Examples 1, 2 and Comparative Example 1 described later, after a specified pulse voltage is applied and the voltage is removed, showing the time change of the luminous intensity of the organic EL elements.

[1985] exist Figure 8A In the chart, the pulse voltage removal time point is used as the origin. Additionally, Figure 8A The graph represents the brightness at voltage removal as 1. After voltage removal, a slow decay component appears up to approximately 4.0E-05 seconds later.

[1986] Figure 8BThe graphs are plotted for the organic EL elements of Examples 1, 2, and Comparative Example 1, with the pulse voltage removal time point as the origin, and plotted as the reciprocal of the square root of the light intensity up to 4.0.E-05 seconds after voltage removal. The fitting was performed as follows.

[1987] For example, in the case of the organic EL element of Example 1, the value of the intersection point A with the vertical axis when the linear portion is extended to the origin of time is 0.9996. Therefore, the luminescence intensity ratio derived from delayed fluorescence obtained from this transition EL waveform exceeds 1 / (0.9996). 2 =0.99. That is, more than 99% originates from delayed fluorescence. That is, it exceeds 37.5% of what is considered the theoretical limit for the TTF ratio. For the organic EL elements of Example 2 and Comparative Example 1, the luminescence intensity ratio originating from delayed fluorescence can also be calculated using the same method as in Example 1.

[1988] Fitting to a straight line is preferably performed using the least squares method. In this case, values ​​between 1.0E-06 seconds and 1.0E-05 seconds are preferably used for fitting.

[1989] (First light-emitting layer)

[1990] The first luminescent layer contains a second host material and a first luminescent compound.

[1991] The second host material is a compound that is different from the first host material. The first luminescent compound is a compound that is different from the first sensitizing material.

[1992] As a second main material, for example, compounds selected from the group consisting of the first and second compounds described later can be cited.

[1993] As a first luminescent compound, for example, at least one compound selected from the group consisting of fluorescent luminescent materials described later, general formula (5), general formula (6) and general formula (3A) can be cited.

[1994] In one embodiment, the first luminescent compound is a compound that exhibits luminescence with a maximum peak wavelength of 430 nm or more and 480 nm or less.

[1995] In one embodiment of this invention, the first luminescent compound is a fluorescent luminescent compound that exhibits fluorescence emission with a maximum peak wavelength of less than 500 nm.

[1996] In one embodiment of this invention, the first luminescent compound is a fluorescent luminescent compound that exhibits fluorescence emission with a maximum peak wavelength of 430 nm or more and 480 nm or less.

[1997] In one embodiment of this invention, the band gap T of the first luminescent compound at 77 [K] is... 77K(D1) and the band gap T at 77 [K] of the second host material 77K (H2) satisfies the following mathematical expression (number 21B).

[1998] T 77K (D1)>T 77K (H2)…(Number 21B)

[1999] By making the first luminescent compound and the second host material satisfy the above mathematical formula (number 21B), when the triplet exciton generated in the first sensitization layer moves to the first luminescent layer, its energy is transferred to the molecules of the second host material, rather than to the first luminescent compound which has a higher triplet energy.

[2000] Furthermore, triplet excitons generated by the recombination of holes and electrons in the second host material do not migrate to the first luminescent compound, which has a higher triplet energy. Triplett excitons generated by recombination in the molecule of the first luminescent compound undergo rapid energy transfer to the molecules of the second host material.

[2001] Triplets of the second host material do not move to the first luminescent compound. Instead, through the TTF phenomenon, the triplets of the second host material collide effectively with each other, thereby generating singlet excitons.

[2002] In one embodiment of this invention, the lowest excitation singlet energy S1(H2) of the second host material and the lowest excitation singlet energy S1(D1) of the first luminescent compound satisfy the following mathematical formula (number 22B).

[2003] S1(H2)>S1(D1)…(Number 22B)

[2004] By making the first luminescent compound and the second host material satisfy the relationship of the mathematical formula (number 22B), the lowest excitation singlet energy S1 of the first luminescent compound is less than the lowest excitation singlet energy S1 of the second host material. Therefore, the singlet excitons generated by the TTF phenomenon transfer energy from the second host material to the first luminescent compound, which helps the first luminescent compound to exhibit fluorescence.

[2005] In one embodiment of this invention, the first luminescent compound is a compound whose molecule does not contain an azazine ring structure.

[2006] In one embodiment of this invention, the first luminescent compound is not a complex.

[2007] In one embodiment of this invention, the first light-emitting layer does not contain metal complexes.

[2008] In one embodiment of this invention, the first light-emitting layer does not contain phosphorescent materials (dopant materials).

[2009] In one embodiment of this invention, the first light-emitting layer does not contain heavy metal complexes or phosphorescent rare earth metal complexes. Examples of heavy metal complexes include iridium complexes, osmium complexes, and platinum complexes.

[2010] In one embodiment of this invention, the first light-emitting layer contains a first luminescent compound at a rate of 0.5% or more by mass or 1% or more by mass of the total mass of the first light-emitting layer.

[2011] In one embodiment, the first light-emitting layer contains a first luminescent compound at a mass percentage of 10% or less, 7% or less, or 5% or less of the total mass of the first light-emitting layer.

[2012] In one embodiment of this scheme, the first light-emitting layer contains the second main material at a mass percentage of 60%, 70%, 80%, 90%, or 95% or more of the total mass of the first light-emitting layer.

[2013] In one embodiment of this scheme, the first light-emitting layer contains a second body material at a mass percentage of less than 99% of the total mass of the first light-emitting layer.

[2014] In one embodiment of this scheme, the upper limit of the total content of the second host material and the first luminescent compound in the first luminescent layer is 100% by mass.

[2015] In one embodiment, the thickness of the first light-emitting layer is 5 nm or more, or 10 nm or more. If the thickness of the first light-emitting layer is 5 nm or more, it is easier to prevent triplet excitons that have migrated from the first sensitization layer to the first light-emitting layer from returning to the first sensitization layer. Furthermore, if the thickness of the first light-emitting layer is 5 nm or more, it is possible to sufficiently distance the triplet excitons from the recombination portion in the first sensitization layer.

[2016] In one embodiment of this invention, the thickness of the first light-emitting layer is 20 nm or less. If the thickness of the first light-emitting layer is 20 nm or less, the density of triplet excitons in the first light-emitting layer can be increased, making the TTF phenomenon more likely to occur.

[2017] (First main material and second main material)

[2018] In one embodiment of this invention, the first host material and the second host material may be exemplified as a first compound represented by the following general formula (1), a first compound represented by the following general formulas (1X), (12X), (13X), (14X), (15X), or (16X), and a second compound represented by the following general formula (2). Furthermore, the first compound may also be used as both the first host material and the second host material. In this case, for convenience, the compound used as the second host material and represented by the aforementioned general formula (1), or the following general formulas (1X), (12X), (13X), (14X), (15X), or (16X) may sometimes be referred to as the second host material.

[2019] In one embodiment of this invention, the first main material is selected from a first compound represented by any one of the following general formulas (1), (1X), (12X), (13X), (14X), (15X), and (16X).

[2020] In one embodiment of this invention, the second main material is selected from a second compound represented by the following general formula (2).

[2021] (First compound)

[2022] In one embodiment of this invention, the first compound is, for example, a compound represented by the following general formula (1), general formula (1X), general formula (12X), general formula (13X), general formula (14X), general formula (15X) or general formula (16X).

[2023] Compounds represented by general formula (1)

[2024] In one embodiment of this invention, the first compound is preferably a compound represented by the following general formula (1). The first compound represented by the following general formula (1) has at least one group represented by the following general formula (11).

[2025] [Chemistry 291]

[2026]

[2027] In the general formula (1),

[2028] R 101 ~R 110 Each independently

[2029] hydrogen atom,

[2030] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2031] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[2032] Alkenes with 2 to 50 carbon atoms, whether substituted or unsubstituted.

[2033] Alkyne groups with 2 to 50 carbon atoms, whether substituted or unsubstituted.

[2034] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2035] With -Si(R 901 (R) 902 (R) 903 () represents a group,

[2036] With -O-(R 904 () represents a group,

[2037] With -S-(R 905 () represents a group,

[2038] Aryl groups, substituted or unsubstituted, having 7 to 50 carbon atoms

[2039] -C(=O)R 801 The group represented

[2040] With -COOR 802 The group represented

[2041] Halogen atoms,

[2042] cyano,

[2043] Nitro,

[2044] substituted or unsubstituted aryl groups with 6 to 50 carbon atoms in the cyclic group

[2045] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or

[2046] The group represented by the general formula (11),

[2047] Among them, R 101 ~R 110 At least one of them is a group represented by the general formula (11).

[2048] In the case where there are multiple groups represented by the general formula (11), the multiple groups represented by the general formula (11) may be the same as or different from each other.

[2049] L 101 for

[2050] single bond,

[2051] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or

[2052] Substituted or unsubstituted divalent heterocyclic groups with 5 to 50 cyclic atoms

[2053] Ar 101 for

[2054] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2055] Heterocyclic groups with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[2056] mx is 0, 1, 2, 3, 4, or 5.

[2057] When there are more than 2 L 101 In the case of 2 or more L 101 Whether they are the same or different,

[2058] In the presence of more than 2 Ar 101 In the case of two or more Ar 101 Whether they are the same or different,

[2059] In the general formula (11), * indicates the position where it bonds with the pyrene ring in the general formula (1).

[2060] In the first compound represented by the general formula (1), R 901 R 902 R 903 R 904 R 905 R 906 R 907 R 801 and R 802 Each independently

[2061] hydrogen atom,

[2062] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2063] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2064] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2065] Heterocyclic groups with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[2066] In the existence of multiple R 901 In the case of multiple R 901 Whether they are the same or different,

[2067] In the existence of multiple R 902 In the case of multiple R 902 Whether they are the same or different,

[2068] In the existence of multiple R 903 In the case of multiple R 903 Whether they are the same or different,

[2069] In the existence of multiple R 904 In the case of multiple R 904 Whether they are the same or different,

[2070] In the existence of multiple R 905 In the case of multiple R 905 Whether they are the same or different,

[2071] In the existence of multiple R 906 In the case of multiple R 906 Whether they are the same or different,

[2072] In the existence of multiple R 907 In the case of multiple R 907 Whether they are the same or different,

[2073] In the existence of multiple R 801 In the case of multiple R 801 Whether they are the same or different,

[2074] In the existence of multiple R 802 In the case of multiple R 802 They are the same or different from each other.

[2075] In one embodiment, Ar is preferred. 101 It is an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.

[2076] In one embodiment, Ar is preferred. 101 for

[2077] Substituted or unsubstituted phenyl

[2078] Substituted or unsubstituted naphthyl groups

[2079] Substituted or unsubstituted biphenyl,

[2080] Substituted or unsubstituted triphenyl,

[2081] Substituted or unsubstituted pyrene,

[2082] Replaced or unreplaced foie gras, or

[2083] Substituted or unsubstituted fluorene group.

[2084] In one embodiment, the first compound is preferably represented by the following general formula (101).

[2085] [Chemistry 292]

[2086]

[2087] (in the general formula (101),

[2088] R 101 ~R 120 Each independently

[2089] hydrogen atom,

[2090] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2091] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[2092] Alkenes with 2 to 50 carbon atoms, whether substituted or unsubstituted.

[2093] Alkyne groups with 2 to 50 carbon atoms, whether substituted or unsubstituted.

[2094] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2095] With -Si(R 901 (R) 902 (R) 903 () represents a group,

[2096] With -O-(R 904 () represents a group,

[2097] With -S-(R 905 () represents a group,

[2098] Aryl groups, substituted or unsubstituted, having 7 to 50 carbon atoms

[2099] -C(=O)R 801 The group represented

[2100] With -COOR 802 The group represented

[2101] Halogen atoms,

[2102] cyano,

[2103] Nitro,

[2104] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2105] Heterocyclic groups with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[2106] Among them, R 101 ~R 110 One of the representations in L 101 The location of the bond, R 111 ~R 120 One of the representations in L101 The location of the bond,

[2107] L 101 for

[2108] single bond,

[2109] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or

[2110] Substituted or unsubstituted divalent heterocyclic groups with 5 to 50 cyclic atoms

[2111] mx is 0, 1, 2, 3, 4, or 5.

[2112] When there are more than 2 L 101 In the case of 2 or more L 101 (They may be the same as or different from each other.)

[2113] In one embodiment, L is preferred. 101 It is a single bond, or a cyclic aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.

[2114] In one embodiment, R is preferred. 101 ~R 110 Two or more of them are groups represented by the general formula (11).

[2115] In one embodiment, R is preferred. 101 ~R 110 Two or more of them are groups represented by the general formula (11), and Ar 101 It is an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.

[2116] In one implementation,

[2117] Preferred Ar 101 Whether pyrene is replaced or not,

[2118] L 101 Not substituted or unsubstituted pyrene,

[2119] R as a group not represented by the general formula (11) 101 ~R 110 The aryl group, whether substituted or unsubstituted, has a cyclic carbon number of 6 to 50 and is not a substituted or unsubstituted pyrene group.

[2120] In one embodiment, it is preferable that the R group is not represented by the general formula (11). 101 ~R 110 Each independently

[2121] hydrogen atom,

[2122] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2123] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2124] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2125] Heterocyclic groups with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[2126] In one embodiment, it is preferable that the R group is not represented by the general formula (11). 101 ~R 110 Each independently

[2127] hydrogen atom,

[2128] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or

[2129] Cycloalkyl groups, substituted or unsubstituted, having a cyclic carbon number of 3 to 50.

[2130] In one embodiment, it is preferable that the R group is not represented by the general formula (11). 101 ~R 110 It is a hydrogen atom.

[2131] Compounds represented by the general formula (1X)

[2132] In one embodiment of this invention, it is also preferred that the first compound is a compound represented by the following general formula (1X).

[2133] [Chemistry 293]

[2134]

[2135] (In the general formula (1X),

[2136] R 101 ~R 112 Each independently

[2137] hydrogen atom,

[2138] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2139] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[2140] Alkenes with 2 to 50 carbon atoms, whether substituted or unsubstituted.

[2141] Alkyne groups with 2 to 50 carbon atoms, whether substituted or unsubstituted.

[2142] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2143] With -Si(R 901 (R) 902 (R) 903 () represents a group,

[2144] With -O-(R 904 () represents a group,

[2145] With -S-(R 905 () represents a group,

[2146] Aryl groups, substituted or unsubstituted, having 7 to 50 carbon atoms

[2147] -C(=O)R 801 The group represented

[2148] With -COOR 802 The group represented

[2149] Halogen atoms,

[2150] cyano,

[2151] Nitro,

[2152] substituted or unsubstituted aryl groups with 6 to 50 carbon atoms

[2153] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or

[2154] Groups represented by the general formula (11X),

[2155] Among them, R 101 ~R 112 At least one of them is a group represented by the general formula (11X),

[2156] In the case where there are multiple groups represented by the general formula (11X), the multiple groups represented by the general formula (11X) may be the same as or different from each other.

[2157] L 101 for

[2158] single bond,

[2159] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or

[2160] Substituted or unsubstituted divalent heterocyclic groups with 5 to 50 cyclic atoms

[2161] Ar 101 for

[2162] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2163] Heterocyclic groups with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[2164] mx is 1, 2, 3, 4 or 5.

[2165] When there are more than 2 L 101 In the case of 2 or more L 101 Whether they are the same or different,

[2166] In the presence of more than 2 Ar 101 In the case of two or more Ar 101 Whether they are the same or different,

[2167] In the general formula (11X), the asterisk (*) indicates the position where it is bonded to the benzo[a]anthracene ring in the general formula (1X).

[2168] In one embodiment of this invention, the group represented by the general formula (11X) is preferably a group represented by the following general formula (111X).

[2169] [Chemistry 294]

[2170]

[2171] (In the general formula (111X),

[2172] X1 is CR 143 R 144 oxygen atom, sulfur atom or NR 145 ,

[2173] L 111 and L 112 Each independently

[2174] single bond,

[2175] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or

[2176] Substituted or unsubstituted divalent heterocyclic groups with 5 to 50 cyclic atoms

[2177] ma is 1, 2, 3, or 4.

[2178] mb is 1, 2, 3, or 4.

[2179] ma+mb is 2, 3, or 4.

[2180] Ar 101 Ar in the general formula (11) 101 Synonyms

[2181] R 141 R 142 R 143 R144 and R 145 Each independently

[2182] hydrogen atom,

[2183] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2184] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[2185] Alkenes with 2 to 50 carbon atoms, whether substituted or unsubstituted.

[2186] Alkyne groups with 2 to 50 carbon atoms, whether substituted or unsubstituted.

[2187] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2188] With -Si(R 901 (R) 902 (R) 903 () represents a group,

[2189] With -O-(R 904 () represents a group,

[2190] With -S-(R 905 () represents a group,

[2191] Aryl groups, substituted or unsubstituted, having 7 to 50 carbon atoms

[2192] -C(=O)R 801 The group represented

[2193] With -COOR 802 The group represented

[2194] Halogen atoms,

[2195] cyano,

[2196] Nitro,

[2197] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2198] Heterocyclic groups with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[2199] mc is 3.

[2200] 3 Rs 141 Whether they are the same or different,

[2201] md is 3

[2202] 3 Rs 142 (They may be the same as or different from each other.)

[2203] In the group represented by the general formula (111X), in the ring structure represented by the following general formula (111aX), L atoms are bonded at any one of the positions *1 to *8 of the carbon atoms in the ring structure represented by the following general formula (111X). 111 R is bonded at the remaining 3 positions from *1 to *4. 141 L is bonded at any one of the positions from *5 to *8. 112 R is bonded at the remaining 3 positions from *5 to *8. 142 .

[2204] [Chemistry 295]

[2205]

[2206] For example, in the group represented by the general formula (111X), L 111 The positions of the carbon atoms *2 and L in the ring structure represented by the general formula (111aX) are bonded. 112 When bonded to the position of the carbon atom at *7 in the ring structure represented by the general formula (111aX), the group represented by the general formula (111X) is represented by the following general formula (111bX).

[2207] [Chemistry 296]

[2208]

[2209] (In the general formula (111bX),

[2210] X1, L 111 L 112 ma, mb, Ar 101 R 141 R 142 R 143 R 144 and R 145 Independently related to X1 and L in the general formula (111X) 111 L 112 ma, mb, Ar 101 R 141 R 142 R 143 R 144 and R 145 Synonyms

[2211] Multiple R 141 Whether they are the same or different,

[2212] Multiple R 142 (They may be the same as or different from each other.)

[2213] In one embodiment of this invention, the group represented by the general formula (111X) is preferably a group represented by the general formula (111bX).

[2214] In compounds represented by the general formula (1X), ma is preferably 1 or 2, and mb is preferably 1 or 2.

[2215] In compounds represented by the general formula (1X), ma is preferably 1 and mb is preferably 1.

[2216] Among the compounds represented by the general formula (1X), Ar is preferred. 101 It is an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.

[2217] Among the compounds represented by the general formula (1X), Ar is preferred. 101 for

[2218] Substituted or unsubstituted phenyl

[2219] Substituted or unsubstituted naphthyl groups

[2220] Substituted or unsubstituted biphenyl,

[2221] Substituted or unsubstituted triphenyl,

[2222] Substituted or unsubstituted benzo[a]anthracene,

[2223] Substituted or unsubstituted pyrene,

[2224] Replaced or unreplaced foie gras, or

[2225] Substituted or unsubstituted fluorene group.

[2226] The compound represented by the general formula (1X) is also preferably represented by the general formula (101X).

[2227] [Chemistry 297]

[2228]

[2229] (In the general formula (101X),

[2230] R 111 and R 112 One of the representations in L 101 The location of the bond, R 133 and R 134 One of the representations in L 101 The location of the bond,

[2231] R 101 ~R 110 R 121 ~R 130Not related to L 101 R of the bond position 111 or R 112 and not related to L 101 R of the bonding position 133 or R 134 Each independently

[2232] hydrogen atom,

[2233] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2234] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[2235] Alkenes with 2 to 50 carbon atoms, whether substituted or unsubstituted.

[2236] Alkyne groups with 2 to 50 carbon atoms, whether substituted or unsubstituted.

[2237] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2238] With -Si(R 901 (R) 902 (R) 903 () represents a group,

[2239] With -O-(R 904 () represents a group,

[2240] With -S-(R 905 () represents a group,

[2241] Aryl groups, substituted or unsubstituted, having 7 to 50 carbon atoms

[2242] -C(=O)R 801 The group represented

[2243] With -COOR 802 The group represented

[2244] Halogen atoms,

[2245] cyano,

[2246] Nitro,

[2247] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2248] Heterocyclic groups with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[2249] L 101 for

[2250] single bond,

[2251] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or

[2252] Substituted or unsubstituted divalent heterocyclic groups with 5 to 50 cyclic atoms

[2253] mx is 1, 2, 3, 4 or 5.

[2254] When there are more than 2 L 101 In the case of 2 or more L 101 (They may be the same as or different from each other.)

[2255] Among the compounds represented by the general formula (1X), L is preferred. 101 for

[2256] single key, or

[2257] A substituted or unsubstituted aryl group with 6 to 50 carbon atoms in a cyclic structure.

[2258] The compound represented by the general formula (1X) is also preferably represented by the general formula (102X).

[2259] [Chemistry 298]

[2260]

[2261] (In the general formula (102X),

[2262] R 111 and R 112 One of the representations in L 111 The location of the bond, R 133 and R 134 One of the representations in L 112 The location of the bond,

[2263] R 101 ~R 110 R 121 ~R 130 Not related to L 111 R of the bonding position 111 or R 112 and not related to L 112 R of the bonding position 133 or R 134 Each independently

[2264] hydrogen atom,

[2265] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2266] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[2267] Alkenes with 2 to 50 carbon atoms, whether substituted or unsubstituted.

[2268] Alkyne groups with 2 to 50 carbon atoms, whether substituted or unsubstituted.

[2269] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2270] With -Si(R 901 (R) 902 (R) 903 () represents a group,

[2271] With -O-(R 904 () represents a group,

[2272] With -S-(R 905 () represents a group,

[2273] Aryl groups, substituted or unsubstituted, having 7 to 50 carbon atoms

[2274] -C(=O)R 801 The group represented

[2275] With -COOR 802 The group represented

[2276] Halogen atoms,

[2277] cyano,

[2278] Nitro,

[2279] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2280] Heterocyclic groups with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[2281] X1 is CR 143 R 144 oxygen atom, sulfur atom or NR 145 ,

[2282] L 111 and L 112 Each independently

[2283] single bond,

[2284] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or

[2285] Substituted or unsubstituted divalent heterocyclic groups with 5 to 50 cyclic atoms

[2286] ma is 1, 2, 3, or 4.

[2287] mb is 1, 2, 3, or 4.

[2288] ma+mb is 2, 3, 4 or 5.

[2289] R 141 R 142 R 143 R 144 and R 145 Each independently

[2290] hydrogen atom,

[2291] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2292] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[2293] Alkenes with 2 to 50 carbon atoms, whether substituted or unsubstituted.

[2294] Alkyne groups with 2 to 50 carbon atoms, whether substituted or unsubstituted.

[2295] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2296] With -Si(R 901 (R) 902 (R) 903 () represents a group,

[2297] With -O-(R 904 () represents a group,

[2298] With -S-(R 905 () represents a group,

[2299] Aryl groups, substituted or unsubstituted, having 7 to 50 carbon atoms

[2300] -C(=O)R 801 The group represented

[2301] With -COOR 802 The group represented

[2302] Halogen atoms,

[2303] cyano,

[2304] Nitro,

[2305] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2306] Heterocyclic groups with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[2307] mc is 3.

[2308] 3 Rs 141 Whether they are the same or different,

[2309] md is 3

[2310] 3 Rs 142 (They may be the same as or different from each other.)

[2311] In compounds represented by the general formula (1X), it is preferred that ma in the general formula (102X) is 1 or 2, and mb is 1 or 2.

[2312] In compounds represented by the general formula (1X), it is preferred that ma is 1 and mb is 1 in the general formula (102X).

[2313] In compounds represented by the general formula (1X), it is also preferred that the group represented by the general formula (11X) is a group represented by the general formula (11AX) or a group represented by the general formula (11BX).

[2314] [Chemistry 299]

[2315]

[2316] (In the general formula (11AX) and the general formula (11BX),

[2317] R 121 ~R 131 Each independently

[2318] hydrogen atom,

[2319] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2320] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[2321] Alkenes with 2 to 50 carbon atoms, whether substituted or unsubstituted.

[2322] Alkyne groups with 2 to 50 carbon atoms, whether substituted or unsubstituted.

[2323] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2324] With -Si(R 901 (R) 902 (R) 903 () represents a group,

[2325] With -O-(R 904 () represents a group,

[2326] With -S-(R 905 () represents a group,

[2327] Aryl groups, substituted or unsubstituted, having 7 to 50 carbon atoms

[2328] -C(=O)R 801 The group represented

[2329] With -COOR 802 The group represented

[2330] Halogen atoms,

[2331] cyano,

[2332] Nitro,

[2333] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2334] Heterocyclic groups with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[2335] In the case where there are multiple groups represented by the general formula (11AX), the multiple groups represented by the general formula (11AX) may be the same as or different from each other.

[2336] In the presence of multiple groups represented by the general formula (11BX), the multiple groups represented by the general formula (11BX) may be the same as or different from each other.

[2337] L 131 and L 132 Each independently

[2338] single bond,

[2339] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or

[2340] Substituted or unsubstituted divalent heterocyclic groups with 5 to 50 cyclic atoms

[2341] In the general formulas (11AX) and (11BX), the asterisk (*) indicates the position where the benzo[a]anthracene ring is bonded to in the general formula (1X).

[2342] The compound represented by the general formula (1X) is also preferably represented by the general formula (103X).

[2343] [Chemical 300]

[2344]

[2345] (In the general formula (103X),

[2346] R 101 ~R 110 and R 112 R in the general formula (1X) respectively 101 ~R 110 and R 112 Synonyms

[2347] R 121 ~R 131 L 131 and L 132 R in the general formula (11BX) respectively 121 ~R 131 L 131 and L 132 Synonyms.

[2348] Among the compounds represented by the general formula (1X), L is also preferred. 131 It is a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in a cyclic structure.

[2349] Among the compounds represented by the general formula (1X), L is also preferred. 132 It is a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in a cyclic structure.

[2350] In compounds represented by the general formula (1X), R is also preferred. 101 ~R 112 Two or more of them are groups represented by the general formula (11).

[2351] In the compound represented by the general formula (1X), R is preferred. 101 ~R 112 Two or more of them are groups represented by the general formula (11X), where Ar in the general formula (11X) 101 It is an aryl group with 6 to 50 carbon atoms, either substituted or unsubstituted.

[2352] In compounds represented by the general formula (1X),

[2353] Ar is also preferred 101 Unsubstituted or unsubstituted benzo[a]anthracene,

[2354] L 101 Unsubstituted or unsubstituted benzo[a]anthracene,

[2355] R is a group that is not represented by the general formula (11X). 101 ~R 110 The substituted or unsubstituted aryl group with 6 to 50 carbon atoms is a non-substituted or unsubstituted benzo[a]anthyl group.

[2356] In compounds represented by the general formula (1X), it is preferable that the R group is not represented by the general formula (11X). 101 ~R 112 Each independently

[2357] hydrogen atom,

[2358] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2359] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2360] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2361] Heterocyclic groups with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[2362] In compounds represented by the general formula (1X), it is preferable that the R group is not represented by the general formula (11X). 101 ~R 112 for

[2363] hydrogen atom,

[2364] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or

[2365] Cycloalkyl groups, substituted or unsubstituted, having a cyclic carbon number of 3 to 50.

[2366] In compounds represented by the general formula (1X), it is preferable that the R group is not represented by the general formula (11X). 101 ~R 112 It is a hydrogen atom.

[2367] Compounds represented by the general formula (12X)

[2368] In one embodiment of this invention, it is also preferred that the first compound is a compound represented by the following general formula (12X).

[2369] [Chemical Engineering 301]

[2370]

[2371] (In the general formula (12X),

[2372] By R 1201 ~R 1210 One or more groups consisting of two or more adjacent elements.

[2373] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[2374] They bond to each other to form substituted or unsubstituted fused rings.

[2375] R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 1201 ~R 1210 Each independently

[2376] hydrogen atom,

[2377] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2378] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[2379] Alkenes with 2 to 50 carbon atoms, whether substituted or unsubstituted.

[2380] Alkyne groups with 2 to 50 carbon atoms, whether substituted or unsubstituted.

[2381] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2382] With -Si(R 901 (R) 902 (R) 903 () represents a group,

[2383] With -O-(R 904 () represents a group,

[2384] With -S-(R 905 () represents a group,

[2385] Aryl groups, substituted or unsubstituted, having 7 to 50 carbon atoms

[2386] -C(=O)R 801 The group represented

[2387] With -COOR 802 The group represented

[2388] Halogen atoms,

[2389] cyano,

[2390] Nitro,

[2391] substituted or unsubstituted aryl groups with 6 to 50 carbon atoms

[2392] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or

[2393] The group represented by the general formula (121),

[2394] Wherein, the substituent in the case of the substituted or unsubstituted monocyclic ring having a substituent, the substituent in the case of the substituted or unsubstituted fused ring having a substituent, and R 1201 ~R 1210 At least one of them is a group represented by the general formula (121),

[2395] In the case where there are multiple groups represented by the general formula (121), the multiple groups represented by the general formula (121) may be the same as or different from each other.

[2396] L1201 for

[2397] single bond,

[2398] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or

[2399] Substituted or unsubstituted divalent heterocyclic groups with 5 to 50 cyclic atoms

[2400] Ar 1201 for

[2401] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2402] Heterocyclic groups with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[2403] mx2 is 0, 1, 2, 3, 4, or 5.

[2404] When there are more than 2 L 1201 In the case of 2 or more L 1201 Whether they are the same or different,

[2405] In the presence of more than 2 Ar 1201 In the case of two or more Ar 1201 Whether they are the same or different,

[2406] In the general formula (121), * indicates the position of the ring bond represented by the general formula (12X).

[2407] In the general formula (12X), R 1201 ~R 1210 In R, a group consisting of two adjacent elements refers to... 1201 With R 1202 group, R 1202 With R 1203 group, R 1203 With R 1204 group, R 1204 With R 1205 group, R 1205 With R 1206 group, R 1207 With R 1208 group, R 1208 With R 1209 The group, and R 1209 With R 1210 The group.

[2408] Compounds represented by the general formula (13X)

[2409] In one embodiment of this invention, it is also preferred that the first compound is a compound represented by the following general formula (13X).

[2410] [Chemical 302]

[2411]

[2412] (In the general formula (13X),

[2413] R 1301 ~R 1310 Each independently

[2414] hydrogen atom,

[2415] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2416] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[2417] Alkenes with 2 to 50 carbon atoms, whether substituted or unsubstituted.

[2418] Alkyne groups with 2 to 50 carbon atoms, whether substituted or unsubstituted.

[2419] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2420] With -Si(R 901 (R) 902 (R) 903 () represents a group,

[2421] With -O-(R 904 () represents a group,

[2422] With -S-(R 905 () represents a group,

[2423] Aryl groups, substituted or unsubstituted, having 7 to 50 carbon atoms

[2424] -C(=O)R 801 The group represented

[2425] With -COOR 802 The group represented

[2426] Halogen atoms,

[2427] cyano,

[2428] Nitro,

[2429] substituted or unsubstituted aryl groups with 6 to 50 carbon atoms

[2430] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or

[2431] The group represented by the general formula (131),

[2432] Among them, R 1301 ~R 1310 At least one of them is a group represented by the general formula (131),

[2433] In the case where there are multiple groups represented by the general formula (131), the multiple groups represented by the general formula (131) may be the same as or different from each other.

[2434] L 1301 for

[2435] single bond,

[2436] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or

[2437] Substituted or unsubstituted divalent heterocyclic groups with 5 to 50 cyclic atoms

[2438] Ar 1301 for

[2439] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2440] Heterocyclic groups with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[2441] mx3 can be 0, 1, 2, 3, 4, or 5.

[2442] When there are more than 2 L 1301 In the case of 2 or more L 1301 Whether they are the same or different,

[2443] In the presence of more than 2 Ar 1301 In the case of two or more Ar 1301 Whether they are the same or different,

[2444] In general formula (131), * indicates the position where it is bonded to the fluoranthene ring in general formula (13X).

[2445] In one embodiment of this invention, R is composed of a group not represented by the general formula (131). 1301 ~R 1310 In this context, groups consisting of two or more adjacent elements are not bonded to each other. In the general formula (13X), a group consisting of two adjacent elements refers to R. 1301 With R 1302 group, R 1302 With R 1303 group, R 1303 With R 1304 group, R 1304 With R 1305 group, R 1305 With R 1306 group, R1307 With R 1308 group, R 1308 With R 1309 The group, and R 1309 With R 1310 The group.

[2446] Compounds represented by the general formula (14X)

[2447] In one embodiment of this invention, it is also preferred that the first compound is a compound represented by the following general formula (14X).

[2448] [Chemical 303]

[2449]

[2450] (In the general formula (14X),

[2451] R 1401 ~R 1410 Each independently

[2452] hydrogen atom,

[2453] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2454] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[2455] Alkenes with 2 to 50 carbon atoms, whether substituted or unsubstituted.

[2456] Alkyne groups with 2 to 50 carbon atoms, whether substituted or unsubstituted.

[2457] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2458] With -Si(R 901 (R) 902 (R) 903 () represents a group,

[2459] With -O-(R 904 () represents a group,

[2460] With -S-(R 905 () represents a group,

[2461] Aryl groups, substituted or unsubstituted, having 7 to 50 carbon atoms

[2462] -C(=O)R 801 The group represented

[2463] With -COOR 802 The group represented

[2464] Halogen atoms,

[2465] cyano,

[2466] Nitro,

[2467] substituted or unsubstituted aryl groups with 6 to 50 carbon atoms in the cyclic group

[2468] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or

[2469] The group represented by the general formula (141),

[2470] Among them, R 1401 ~R 1410 At least one of them is a group represented by the general formula (141),

[2471] In the case where there are multiple groups represented by the general formula (141), the multiple groups represented by the general formula (141) may be the same as or different from each other.

[2472] L 1401 for

[2473] single bond,

[2474] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or

[2475] Substituted or unsubstituted divalent heterocyclic groups with 5 to 50 cyclic atoms

[2476] Ar 1401 for

[2477] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2478] Heterocyclic groups with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[2479] mx4 can be 0, 1, 2, 3, 4, or 5.

[2480] When there are more than 2 L 1401 In the case of 2 or more L 1401 Whether they are the same or different,

[2481] In the presence of more than 2 Ar 1401 In the case of two or more Ar 1401 Whether they are the same or different,

[2482] In the general formula (141), * indicates the position of the ring bond represented by the general formula (14X).

[2483] Compounds represented by the general formula (15X)

[2484] In one embodiment of this invention, it is also preferred that the first compound is a compound represented by the following general formula (15X).

[2485] [Chemical 304]

[2486]

[2487] (In the general formula (15X),

[2488] R 1501 ~R 1514 Each independently

[2489] hydrogen atom,

[2490] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2491] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[2492] Alkenes with 2 to 50 carbon atoms, whether substituted or unsubstituted.

[2493] Alkyne groups with 2 to 50 carbon atoms, whether substituted or unsubstituted.

[2494] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2495] With -Si(R 901 (R) 902 (R) 903 () represents a group,

[2496] With -O-(R 904 () represents a group,

[2497] With -S-(R 905 () represents a group,

[2498] Aryl groups, substituted or unsubstituted, having 7 to 50 carbon atoms

[2499] -C(=O)R 801 The group represented

[2500] With -COOR 802 The group represented

[2501] Halogen atoms,

[2502] cyano,

[2503] Nitro,

[2504] substituted or unsubstituted aryl groups with 6 to 50 carbon atoms

[2505] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or

[2506] The group represented by the general formula (151),

[2507] Among them, R 1501 ~R 1514 At least one of them is a group represented by the general formula (151),

[2508] In the case where there are multiple groups represented by the general formula (151), the multiple groups represented by the general formula (151) may be the same as or different from each other.

[2509] L 1501 for

[2510] single bond,

[2511] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or

[2512] Substituted or unsubstituted divalent heterocyclic groups with 5 to 50 cyclic atoms

[2513] Ar 1501 for

[2514] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2515] Heterocyclic groups with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[2516] mx5 can be 0, 1, 2, 3, 4, or 5.

[2517] When there are more than 2 L 1501 In the case of 2 or more L 1501 Whether they are the same or different,

[2518] In the presence of more than 2 Ar 1501 In the case of two or more Ar 1501 Whether they are the same or different,

[2519] In the general formula (151), * indicates the position of the ring bond represented by the general formula (15X).

[2520] Compounds represented by the general formula (16X)

[2521] In one embodiment of this invention, it is also preferred that the first compound is a compound represented by the following general formula (16X).

[2522] [Chemical 305]

[2523]

[2524] (In the general formula (16X),

[2525] R1601 ~R 1614 Each independently

[2526] hydrogen atom,

[2527] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2528] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[2529] Alkenes with 2 to 50 carbon atoms, whether substituted or unsubstituted.

[2530] Alkyne groups with 2 to 50 carbon atoms, whether substituted or unsubstituted.

[2531] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2532] With -Si(R 901 (R) 902 (R) 903 () represents a group,

[2533] With -O-(R 904 () represents a group,

[2534] With -S-(R 905 () represents a group,

[2535] Aryl groups, substituted or unsubstituted, having 7 to 50 carbon atoms

[2536] -C(=O)R 801 The group represented

[2537] With -COOR 802 The group represented

[2538] Halogen atoms,

[2539] cyano,

[2540] Nitro,

[2541] substituted or unsubstituted aryl groups with 6 to 50 carbon atoms in the cyclic group

[2542] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms, or

[2543] The group represented by the general formula (161),

[2544] Among them, R 1601 ~R 1614 At least one of them is a group represented by the general formula (161),

[2545] In the case where there are multiple groups represented by the general formula (161), the multiple groups represented by the general formula (161) may be the same as or different from each other.

[2546] L 1601 for

[2547] single bond,

[2548] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or

[2549] Substituted or unsubstituted divalent heterocyclic groups with 5 to 50 cyclic atoms

[2550] Ar 1601 for

[2551] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2552] Heterocyclic groups with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[2553] mx6 can be 0, 1, 2, 3, 4, or 5.

[2554] When there are more than 2 L 1601 In the case of 2 or more L 1601 Whether they are the same or different,

[2555] In the presence of more than 2 Ar 1601 In the case of two or more Ar 1601 Whether they are the same or different,

[2556] In the general formula (161), * indicates the position of the ring bond represented by the general formula (16X).

[2557] In one embodiment, the first host material preferably has a linking structure in the molecule comprising a benzene ring and a naphthalene ring connected by a single bond, wherein the benzene ring and the naphthalene ring in the linking structure are further independently condensed or not condensed with a single ring or a fused ring, and the benzene ring and the naphthalene ring in the linking structure are further connected by crosslinking at least one part other than the single bond.

[2558] By giving the first host material a cross-linked connection structure, it is expected that the color degradation of organic EL elements can be suppressed.

[2559] In this case, the first host material only needs to have a linkage structure (sometimes called a benzene-naphthalene linkage structure) in the molecule, represented by formula (X1) or formula (X2), as the smallest unit. A single ring or a fused ring can be further condensed on the benzene ring, or a single ring or a fused ring can be further condensed on the naphthalene ring. For example, even if the first host material has a linkage structure (sometimes called a naphthalene-naphthalene linkage structure), represented by formula (X3), formula (X4), or formula (X5), in the molecule, since one of the naphthalene rings contains a benzene ring, it also contains a benzene-naphthalene linkage structure.

[2560] [Chemical 306]

[2561]

[2562] In one embodiment of this invention, it is further preferred that the crosslinking comprises double bonds. That is,

[2563] It is also preferred that the structure is formed by further connecting the benzene ring and the naphthalene ring in the portion other than the single bond through a cross-linking structure containing double bonds.

[2564] If the benzene ring and naphthalene ring in the benzene-naphthalene linkage structure are further linked by crosslinking at least one part other than the single bond, then, for example, in the case of formula (X1), it becomes a linkage structure (fused ring) represented by formula (X11), and in the case of formula (X3), it becomes a linkage structure (fused ring) represented by formula (X31).

[2565] If the benzene ring and naphthalene ring in the benzene-naphthalene linkage structure are further linked in the portion other than the single bond through crosslinking including double bonds, then, for example, in the case of formula (X1), it becomes a linkage structure (fused ring) represented by formula (X12); in the case of formula (X2), it becomes a linkage structure (fused ring) represented by formula (X21) or formula (X22); in the case of formula (X4), it becomes a linkage structure (fused ring) represented by formula (X41); and in the case of formula (X5), it becomes a linkage structure (fused ring) represented by formula (X51).

[2566] If the benzene ring and naphthalene ring in the benzene-naphthalene linkage structure are further linked in at least one part other than the single bond by crosslinking containing heteroatoms (e.g., oxygen atoms), then, for example, in the case of formula (X1), it becomes a linkage structure (fused ring) represented by the following formula (X13).

[2567] [Chemical 307]

[2568]

[2569] In one embodiment of this invention, it is also preferred that the first host material has a biphenyl structure in the molecule in which a first benzene ring and a second benzene ring are connected by a single bond, and the first benzene ring and the second benzene ring in the biphenyl structure are further connected by crosslinking in at least one part other than the single bond.

[2570] In one embodiment of this invention, it is further preferred that the first benzene ring and the second benzene ring in the biphenyl structure are further connected through crosslinking in a portion other than the single bond. By giving the first host material a biphenyl structure comprising such crosslinking, it is expected to suppress color degradation of the organic EL element.

[2571] In one embodiment of this invention, it is also preferred that the crosslinking comprises double bonds.

[2572] In one embodiment of this invention, it is also preferred that the crosslinking does not contain double bonds.

[2573] Preferably, the first benzene ring and the second benzene ring in the biphenyl structure are further connected in the two parts other than the single bond through the crosslinking.

[2574] In one embodiment of this invention, it is further preferred that the first and second benzene rings in the biphenyl structure are further connected in the two portions other than the single bond through the crosslinking, and that the crosslinking does not contain double bonds. By giving the first host material a biphenyl structure containing such crosslinking, it is expected to suppress the color degradation of the organic EL element.

[2575] For example, if the first benzene ring and the second benzene ring in the biphenyl structure represented by the following formula (BP1) are further linked by crosslinking in at least one part other than the single bond, the biphenyl structure becomes a linked structure (fused ring) such as the following formulas (BP11) to (BP15).

[2576] [Chemical 308]

[2577]

[2578] The formula (BP11) is a structure in which one part other than the single bond is linked by crosslinking without double bonds.

[2579] The formula (BP12) is a structure in which one part other than the single bond is connected by crosslinking that includes a double bond.

[2580] The formula (BP13) is a structure in which the two parts other than the single bond are connected by crosslinking without double bonds.

[2581] Formula (BP14) is a structure in which one of the two parts other than the single bond is connected by crosslinking without double bonds, and the other part of the two parts other than the single bond is connected by crosslinking containing double bonds.

[2582] The formula (BP15) is a structure in which the two parts other than the single bond are connected by cross-linking that includes a double bond.

[2583] In the first compound, groups described as "substituted or unsubstituted" are preferably "unsubstituted".

[2584] (Method for manufacturing the first compound)

[2585] The first compound can be produced by known methods. Furthermore, the first compound can also be produced by imitating known methods, using known alternative reactions and starting materials that match the target compound.

[2586] (Specific examples of the first compound)

[2587] Specific examples of the first compound include the following compounds. However, the present invention is not limited to these specific examples of the first compound.

[2588] In this specification, in the specific examples of compounds, D represents a deuterium atom, Me represents a methyl group, and tBu represents a tert-butyl group.

[2589] [Chemical 309]

[2590]

[2591] [Chemical 310]

[2592]

[2593] [Chemistry 311]

[2594]

[2595] [Chemistry 312]

[2596]

[2597] [Chemistry 313]

[2598]

[2599] [Chemical 314]

[2600]

[2601] [Chemical 315]

[2602]

[2603] [Chemistry 316]

[2604]

[2605] [Chemistry 317]

[2606]

[2607] [Chemistry 318]

[2608]

[2609] [Chemistry 319]

[2610]

[2611] [Chemistry 320]

[2612]

[2613] [Chemistry 321]

[2614]

[2615] [Chemistry 322]

[2616]

[2617] [Chemistry 323]

[2618]

[2619] [Chemistry 324]

[2620]

[2621] [Chemistry 325]

[2622]

[2623] (Second compound)

[2624] In one embodiment of this invention, a second compound represented by general formula (2) will be described.

[2625] [Chemistry 326]

[2626]

[2627] (in the general formula (2),

[2628] R 201 ~R 208 Each independently

[2629] hydrogen atom,

[2630] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2631] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[2632] Alkenes with 2 to 50 carbon atoms, whether substituted or unsubstituted.

[2633] Alkyne groups with 2 to 50 carbon atoms, whether substituted or unsubstituted.

[2634] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2635] With -Si(R 901 (R) 902 (R) 903 () represents a group,

[2636] With -O-(R 904 () represents a group,

[2637] With -S-(R 905 () represents a group,

[2638] With -N(R 906 (R) 907 () represents a group,

[2639] Aryl groups, substituted or unsubstituted, having 7 to 50 carbon atoms

[2640] -C(=O)R 801 The group represented

[2641] With -COOR 802 The group represented

[2642] Halogen atoms,

[2643] cyano,

[2644] Nitro,

[2645] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2646] Heterocyclic groups with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[2647] L 201 and L 202 Each independently

[2648] single bond,

[2649] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or

[2650] Substituted or unsubstituted divalent heterocyclic groups with 5 to 50 cyclic atoms

[2651] Ar 201 and Ar 202 Each independently

[2652] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2653] (A heterocyclic group, with 5 to 50 cyclic atoms, either substituted or unsubstituted.)

[2654] (In the second compound of this embodiment, R) 901 R 902 R 903 R 904 R 905 R 906 R 907 R 801 and R 802 Each independently

[2655] hydrogen atom,

[2656] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2657] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2658] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2659] Heterocyclic groups with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[2660] In the existence of multiple R 901 In the case of multiple R 901 Whether they are the same or different,

[2661] In the existence of multiple R 902 In the case of multiple R 902 Whether they are the same or different,

[2662] In the existence of multiple R 903 In the case of multiple R 903 Whether they are the same or different,

[2663] In the existence of multiple R 904 In the case of multiple R 904 Whether they are the same or different,

[2664] In the existence of multiple R 905 In the case of multiple R 905 Whether they are the same or different,

[2665] In the existence of multiple R 906 In the case of multiple R 906 Whether they are the same or different,

[2666] In the existence of multiple R 907 In the case of multiple R 907 Whether they are the same or different,

[2667] In the existence of multiple R 801 In the case of multiple R 801 Whether they are the same or different,

[2668] In the existence of multiple R 802 In the case of multiple R 802 (They may be the same as or different from each other.)

[2669] In one implementation,

[2670] Preferred L 201 and L 202 Each independently

[2671] single key, or

[2672] substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms.

[2673] Ar 201 and Ar 202 Each is independently a substituted or unsubstituted aryl group with a cyclic carbon number of 6 to 50.

[2674] In one embodiment, Ar is preferred. 201 and Ar 202 Each independently

[2675] phenyl,

[2676] Naphthyl,

[2677] Fiki,

[2678] Biphenyl,

[2679] Triphenyl

[2680] Diphenylfluorenyl,

[2681] Dimethylfluorenyl,

[2682] benzodiphenylfluorenyl,

[2683] benzodimethylfluorenyl,

[2684] Dibenzofuranyl,

[2685] Dibenzothiophene group,

[2686] Naphthobenzofuranyl, or

[2687] Naphthobenzothiophene group.

[2688] In one embodiment, preferably in the second compound represented by the general formula (2), R 201 ~R 208 Each independently

[2689] hydrogen atom,

[2690] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2691] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms, or

[2692] With -Si(R 901 (R) 902 (R) 903 () represents a group.

[2693] In one embodiment, L is preferred. 201 for

[2694] single key, or

[2695] Unsubstituted arylene groups with 6–22 cyclic carbon atoms,

[2696] Ar 201 It is an aryl group with 6 to 22 carbon atoms, either substituted or unsubstituted.

[2697] In one embodiment, preferably in the second compound represented by the general formula (2), R 201 ~R 208 Each independently

[2698] hydrogen atom,

[2699] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2700] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms, or

[2701] With -Si(R 901 (R) 902 (R) 903 () represents a group.

[2702] In one embodiment, preferably in the second compound represented by the general formula (2), R 201 ~R 208 It is a hydrogen atom.

[2703] In one embodiment, the second compound is preferably L in the general formula (2). 202 For single bond, Ar 202 Compounds containing unsubstituted phenyl groups.

[2704] In one embodiment, the second compound is preferably L in the general formula (2).202 For single bond, Ar 202 It is a compound with an unsubstituted 2-naphthyl group.

[2705] In one embodiment, the second compound is preferably L in the general formula (2). 202 For single bond, Ar 202 It is a compound with an unsubstituted 1-naphthyl group.

[2706] In one embodiment, the second compound is preferably L in the general formula (2). 202 For unsubstituted p-phenylene, Ar 202 Compounds containing unsubstituted phenyl groups.

[2707] In one embodiment, the second compound is preferably L in the general formula (2). 202 For unsubstituted m-phenylene, Ar 202 Compounds containing unsubstituted phenyl groups.

[2708] In one embodiment, the second compound is preferably L in the general formula (2). 202 For unsubstituted o-phenylene, Ar 202 Compounds containing unsubstituted phenyl groups.

[2709] In one embodiment, the second compound is preferably L in the general formula (2). 202 For unsubstituted p-phenylene, Ar 202 It is a compound with an unsubstituted 1-naphthyl group.

[2710] In one embodiment, the second compound is preferably L in the general formula (2). 202 For unsubstituted p-phenylene, Ar 202 It is a compound with an unsubstituted 2-naphthyl group.

[2711] In one embodiment, the second compound is preferably L in the general formula (2). 202 For unsubstituted 1,4-naphthyl, Ar 202 Compounds containing unsubstituted phenyl groups.

[2712] In one embodiment, the second compound is preferably L in the general formula (2). 202 For unsubstituted m-phenylene, Ar 202 It is a compound with an unsubstituted 2-naphthyl group.

[2713] In one embodiment, the second compound is preferably a compound represented by the following general formula (2X).

[2714] [Chemistry 327]

[2715]

[2716] (In the general formula (2X),

[2717] R 201 and R 203 ~R 208 Independently related to R in the general formula (2) 201 and R 203 ~R 208 Synonyms

[2718] L 201 L 202 Ar 201 and Ar 202 respectively with L in the general formula (2) 201 L 202 Ar 201 and Ar 202 Synonyms

[2719] L 203 L in the general formula (2) 201 Synonyms

[2720] L 201 L 202 and L 203 Whether they are the same or different,

[2721] Ar 203 Ar in the general formula (2) 201 Synonyms

[2722] Ar 201 Ar 202 and Ar 203 (They may be the same as or different from each other.)

[2723] In one embodiment, the second compound is preferably L of the general formula (2X). 202 For single bond, Ar 202 Compounds containing unsubstituted phenyl groups.

[2724] In one embodiment, the second compound is preferably L of the general formula (2X). 202 For single bond, Ar 202 It is a compound with an unsubstituted 2-naphthyl group.

[2725] In one embodiment, the second compound is preferably L in the general formula (2X). 202 For single bond, Ar 202 It is a compound with a...

Claims

1. An organic electroluminescent element, characterized in that: Having: an anode; cathode; a light emitting region disposed between the anode and the cathode, The light-emitting region includes a first sensitizing layer and a first light-emitting layer. The first sensitizing layer contains a first host material and a first sensitizing material, The first light-emitting layer contains a second host material and a first light-emitting compound, The first host material and the second host material are different from each other, The first sensitizing material and the first luminescent compound are different from each other, The lowest excited singlet energy S1(G1) of the first sensitizing material is equal to the energy gap T of the first sensitizing material at 77[K] 77K The difference ΔST(G1) between (G1) and (G1) satisfies the following mathematical formula (Equation 1): ΔST(G1)=S1(G1)-T 77K (G1)<0.5 eV…(Number 1).

2. The organic electroluminescent element according to claim 1, wherein The first sensitizing material does not contain heavy metal elements.

3. The organic electroluminescent element according to claim 1 or 2, characterized in that: The energy gap T of the first sensitizing material at 77[K] 77K (G1), energy gap T of the first host material at 77[K] 77K (H1) and the energy gap T at 77[K] of the second host material 77K (H2) satisfies the following mathematical formula (2): T 77K (G1)>T 77K (H1)>T 77K (H2)…(Number 2).

4. The organic electroluminescent element according to claim 3, wherein: The energy gap T of the first sensitizing material at 77[K] 77K (G1) and the energy gap T of the first host material at 77[K] 77K (H1) satisfies the following mathematical formula (21), T 77K (G1)-T 77K (H1)<0.5 eV…(Equation 21).

5. The organic electroluminescent element according to claim 3 or 4, characterized in that: The energy gap T of the first host material at 77[K] 77K (H1) and the energy gap T of the second host material at 77[K] 77K (H2) satisfies the following mathematical formula (22): T 77K (H1)-T 77K (H2)<0.3eV…(Number 22).

6. The organic electroluminescent element according to any one of claims 1 to 5, wherein: The lowest excited singlet energy S1(G1) of the first sensitizing material and the lowest excited singlet energy S1(BD1) of the first luminescent compound satisfy the relationship of the following mathematical formula (Formula 3): S1(BD1)>S1(G1)…(Number 3).

7. The organic electroluminescent device according to any one of claims 1 to 6, wherein: The first sensitizing layer is directly connected to the first light-emitting layer.

8. The organic electroluminescent device according to any one of claims 1 to 7, wherein: The first sensitizing layer is disposed between the anode and the cathode. The first light-emitting layer is disposed between the first sensitizing layer and the cathode.

9. The organic electroluminescent element according to claim 8, wherein: The absolute value of the lowest unoccupied molecular orbital energy level LUMO (G1) of the first sensitizing material and the absolute value of the lowest unoccupied molecular orbital energy level LUMO (H1) of the first host material satisfy the relationship of the following mathematical formula (Formula 4): |LUMO(G1)|>|LUMO(H1)|…(Number 4).

10. The organic electroluminescent element according to claim 8 or 9, characterized in that: The absolute value of the lowest unoccupied molecular orbital energy level LUMO (H2) of the second host material and the absolute value of the lowest unoccupied molecular orbital energy level LUMO (BD1) of the first luminescent compound satisfy the relationship of the following mathematical formula (Formula 41): |LUMO(H2)|>|LUMO(BD1)|…(number 41).

11. The organic electroluminescent device according to any one of claims 1 to 7, wherein: The first sensitizing layer is disposed between the anode and the cathode. The first light-emitting layer is disposed between the first sensitizing layer and the anode.

12. The organic electroluminescent element according to claim 11, wherein: The absolute value of the highest occupied molecular orbital energy level HOMO (G1) of the first sensitizing material and the absolute value of the highest occupied molecular orbital energy level HOMO (H1) of the first host material satisfy the relationship of the following mathematical formula (Formula 5): |HOMO(G1)|<|HOMO(H1)|…(Number 5).

13. The organic electroluminescent element according to claim 11 or 12, characterized in that: The absolute value of the highest occupied molecular orbital energy level HOMO (H2) of the second host material and the absolute value of the highest occupied molecular orbital energy level HOMO (BD1) of the first luminescent compound satisfy the relationship of the following mathematical formula (Formula 51): |HOMO(H2)|<|HOMO(BD1)|…(Number 51).

14. The organic electroluminescent device according to any one of claims 1 to 13, wherein: In the organic electroluminescent element, the energy E of the peak of the emission spectrum PE (eV) and 0.01cd / m 2 The energy E given to the component when the brightness TH The difference in (eV) satisfies the following mathematical formula (6): E TH -E PE ≤0.05 eV…(Equation 6).

15. The organic electroluminescent device according to any one of claims 1 to 14, wherein: When the light-emitting region is caused to emit light, a delayed fluorescence ratio is greater than 37.5%.

16. The organic electroluminescent device according to any one of claims 1 to 7, wherein: It has: a first light-emitting unit, including the light-emitting area as a first light-emitting area; A first charge generation layer is disposed between the first light emitting unit and the cathode; A second light emitting unit includes a second light emitting region disposed between the first charge generating layer and the cathode, The first light-emitting region includes the first sensitizing layer and the first light-emitting layer, The second light emitting region at least includes a second light emitting layer, The anode, the first light-emitting region, the first charge generation layer, the second light-emitting region and the cathode are arranged in sequence. The second light-emitting layer contains a third host material and a second light-emitting compound.

17. The organic electroluminescent device according to any one of claims 1 to 7, wherein: It has: a first light-emitting unit, including the light-emitting area as a first light-emitting area; A first charge generation layer is disposed between the first light emitting unit and the anode; A second light emitting unit includes a second light emitting region disposed between the first charge generating layer and the anode, The first light-emitting region includes the first sensitizing layer and the first light-emitting layer, The second light emitting region at least includes a second light emitting layer, The anode, the second light-emitting region, the first charge generation layer, the first light-emitting region and the cathode are arranged in sequence, The second light-emitting layer contains a third host material and a second light-emitting compound.

18. The organic electroluminescent element according to claim 16 or 17, wherein: The second light emitting region includes a second sensitizing layer and the second light emitting layer, The first light-emitting region is provided with the first sensitizing layer and the first light-emitting layer in order from the anode side. The second light-emitting region is provided with the second sensitizing layer and the second light-emitting layer in order from the anode side. The second sensitizing layer contains a fourth host material and a second sensitizing material, The third host material and the fourth host material are different from each other, The second sensitizing material and the second luminescent compound are different from each other, The lowest excited singlet energy S1(G2) of the second sensitizing material is equal to the energy gap T of the second sensitizing material at 77[K] 77K The difference ΔST(G2) between (G2) and (G2) satisfies the following mathematical formula (Equation 1A): ΔST(G2) = S1(G2) - T 77K (G2) < 0.5 eV…(Equation 1A).

19. The organic electroluminescent element according to claim 16 or 17, characterized in that: The second light emitting region includes a second sensitizing layer and the second light emitting layer, The first light-emitting region is provided with the first light-emitting layer and the first sensitizing layer in order from the anode side. The second light-emitting region is provided with the second light-emitting layer and the second sensitizing layer in order from the anode side. The second sensitizing layer contains a fourth host material and a second sensitizing material, The third host material and the fourth host material are different from each other, The second sensitizing material and the second luminescent compound are different from each other, The lowest excited singlet energy S1(G2) of the second sensitizing material is equal to the energy gap T of the second sensitizing material at 77[K] 77K The difference ΔST(G2) between (G2) and (G2) satisfies the following mathematical formula (Equation 1A): ΔST(G2) = S1(G2) - T 77K (G2) < 0.5 eV…(Equation 1A).

20. The organic electroluminescent element according to claim 18 or 19, characterized in that: In a second evaluation element in which a light-emitting region having the same structure as the second light-emitting region is sandwiched between the anode and the cathode, when the second evaluation element is made to emit light, the energy E of the peak of the light emission spectrum is PE2 (eV) and 0.01cd / m 2 The energy E given to the second evaluation element when the brightness is TH2 The difference in (eV) satisfies the following mathematical formula (62): E TH2 -E PE2 ≤0.05 eV…(Equation 62).

21. The organic electroluminescent element according to any one of claims 18 to 20, characterized in that: In the second evaluation element in which a light-emitting region having the same structure as the second light-emitting region is sandwiched between the anode and the cathode, when the second evaluation element is made to emit light, a delayed fluorescence ratio is greater than 37.5%.

22. The organic electroluminescent element according to any one of claims 18 to 21, characterized in that: In a first evaluation element in which a light-emitting region having the same structure as the first light-emitting region is sandwiched between the anode and the cathode, when the first evaluation element is made to emit light, the energy E of the peak of the light emission spectrum is PE1 (eV) and 0.01cd / m 2 The energy E given to the first evaluation element when the brightness is TH1 The difference in (eV) satisfies the following mathematical formula (61): E TH1 -E PE1 ≤0.05 eV…(Equation 61).

23. The organic electroluminescent element according to any one of claims 18 to 22, wherein: In the first evaluation element in which a light-emitting region having the same structure as the first light-emitting region is sandwiched between the anode and the cathode, when the first evaluation element is made to emit light, a delayed fluorescence ratio is greater than 37.5%.

24. The organic electroluminescent element according to any one of claims 18 to 23, wherein: The second sensitizing material is a delayed fluorescent material.

25. The organic electroluminescent device according to any one of claims 1 to 24, characterized in that: The first sensitizing material is a delayed fluorescent material.

26. An organic electroluminescent device, characterized in that: A device comprising the organic electroluminescent element according to any one of claims 1 to 25 and a power source, The power source includes a power generation element that generates a potential difference or a current in response to an external stimulus.

27. An electronic device, characterized in that: The organic electroluminescent element according to any one of claims 1 to 25 or the organic electroluminescent device according to claim 26 is mounted.

28. A luminous body comprising a first sensitizing portion and a first luminous portion, characterized in that: The first sensitizing part contains a first host material and a first sensitizing material, The first light-emitting part contains a second host material and a first light-emitting compound, The first host material and the second host material are different from each other, The first sensitizing material and the first luminescent compound are different from each other, The lowest excited singlet energy S1(G1) of the first sensitizing material is equal to the energy gap T of the first sensitizing material at 77[K] 77K The difference ΔST(G1) between (G1) and (G1) satisfies the following mathematical formula (Equation 1): The energy gap T of the first sensitizing material at 77[K] 77K (G1), energy gap T of the first host material at 77[K] 77K (H1) and the energy gap T at 77[K] of the second host material 77K (H2) satisfies the following mathematical formula (2): The lowest excited singlet energy S1(G1) of the first sensitizing material and the lowest excited singlet energy S1(BD1) of the first luminescent compound satisfy the relationship of the following mathematical formula (Formula 3): ΔST(G1)=S1(G1)-T 77K (G1)<0.5 eV…(Number 1) T 77K (G1)>T 77K (H1)>T 77K (H2)…(Number 2) S1(BD1)>S1(G1)…(Number 3).

29. The luminous body according to claim 28, characterized in that The first sensitizing portion is composed of a first sensitizing layer, and the first light-emitting portion is composed of a first light-emitting layer.

30. The luminous body according to claim 29, characterized in that The first sensitizing layer and the first light-emitting layer are used as one repeating unit, and have a stacked structure in which two or more repeating units are stacked.

31. A solar cell, characterized in that: A light emitting body according to any one of claims 28 to 30 is mounted.

32. A light sensor, characterized in that: A light emitting body according to any one of claims 28 to 30 is mounted.

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